Hello experienced SDs,

I've been orbiting the sugar lifestyle for a little while now and this forum has been extremely informative. Anyway, I've finally decided I'd like to dip my toes in the water, but I was curious about some logistical questions.

1) I've read the consensus is that hotels are almost always the way to go. I'm unmarried, so my house would be an option, but it sounds like the risks outweigh the advantages. That said, what's the best way to handle hotel arrangements? Reserve the hotel in my name? Give money to the SB and have her reserve it (and allow her the benefit of the room until check out the next day)? ...then again, that also sounds risky. Just figuring out what's worked well and what horror stories I  can expect either way

2) Despite many people advising to keep things on a PPM basis, I'm actually mostly attracted to the sugar world because of the elimination of the transactional relationship. I'm all about the illusion of a "relationship" without the ironclad strings that come along with civy relationships. That said, my preference is to start off with PPM until I find someone I connect with and then, ideally, switch over to a monthly donation. I know the risks here and am willing to accept it (worst case, I get conned out of a month's worth of sugar; que sera sera). However, I'm curious about logistics re: handling the regular donation. I'm not averse to withdrawing a grand or two in cash each month, but it does seem a little unwieldy. Have you guys tried other payment methods like PayPal or Venmo? Do large, regular amounts of sugar trigger unwanted scrutiny from the IRS or DHS (I don't want some Fed to think I'm funding a terrorist cell or something)? For those of you doing the regular, monthly donation thing, how have you been handling it?

3) In your experience, how long do your a) average and b) best/unicorn sugar relationships tend to last? Ideally, I'd like something in the middle ground: at least a few months to establish and cement chemistry, but not too long to prevent things from getting stale.

Thanks, gentlemen. And, though I try to keep track of this forum regularly, if any of my questions have been answered before, my apologies in advance. I'll go back and "read the fucking manual." :P

Welcome to the Sugar Bowl! Get ready for a wild ride (pun intended).  
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Don't get ahead of yourself as you start to explore.  
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If you prefer a hotel to using your home, you have a few options to make this work. Book ahead, or book as needed: If she's local to you, scout out a few budget hotels in your area on your favorite booking app and look for places which tend to have moderate or lower occupancy rates (so they are likely to have a room available now), decent prices, preferably a direct path to your room that does not require passing by the front desk, and are generally clean and safe. In other words, stay away from 5 stars on one end and hooker pads on the other. Then if you get to a BCD agreement, you can usually book on the spot using your phone, or book a day ahead if you're meeting later in the week. Or do what I do and take her (or give her the address) to your place and fuck her silly.  I'd suggest NOT giving her money to book the hotel or asking her to book then reimbursing her. She may not have a credit card or enough open credit on her card (she's here for cash, remember?), or she might have a BF/Hubby who might see her activity on the bill.  And you face some risk that if you let her "use" the room before/after you are there she will order room service, stay extra days (to host other SD's?) or damage/trash the room leaving you with a surprise bill.  If you need to travel to another city to see her, you will need to book a room anyway, unless she will be hosting you. Pick a room based on your travel needs, not hers.
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Next, if you are paranoid about the money, set up a new checking account and credit card (and debit card) specifically for Sugar spend. You can only lose as much money as you put into the account (with some exceptions). Do not give her a card - it's just a bottomless glass of sugar for her and she will drink deep and often. And if she abuses the card, the negative credit experience goes on your credit report!  
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I'd stick with cash at first. It's simple and easy. PayPal and Venmo are a decent alternative, unless they find you are, or she is, using it for what might be considered purposes that violate their terms of service. Never give her you bank account or card numbers, of course. Unless you are spending way too much on sugar (say over $5k a month to start) don't worry about how your activity looks. It's not likely to trigger questions from your bank. Unless your new SB is actually a crime/drug lord or terrorist! :p  
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As to how long, YMMV is the best advice I can give you.  But please share your experiences so we can all learn.

Bad as that is, it's not the worst case. Imo, the worst thing about a monthly allowance is that it creates feelings of obligation on her part and entitlement on yours, both of which poison the arrangement. She may not be interested at some point but she feels she took your money so she's obligated to see you. You may prefer to do or see someone else, but dammit, you paid her so you are entitled to her company and she damn well better show up!  Bad feelings, bad options.  But if you stick to a gift per visit arrangement it's much more likely that each time you visit you will both be equally, sincerely eager to see each other. And in that scenario, the gift given does not feel transactional at all. I've been doing this with all my SBs, one is over the one year mark, one other is past two years. And it's still fresh and fun.

Monthly creates feelings of obligation and entitlement. So absolutely true.

you're not dealing with professionals, well, most of the time you're not.  I never would trust em to deal with getting a room.  I'm single so my private residence works just fine, rather give the price of a room to the SB and keep em happy.  The m&g is so important to get a feel for how things will go.  I was surprised when I started playing in the sugar bowl how quickly some SB's are ready to come visit you, or join you at a hotel.  Especially after they have had a successful interlude with a SD, they sort of throw caution to the wind.  Also, I would never promise a monthly allowance, only gift per visit.  Lots of reasons why, but in my area the pickings are pretty extensive and it is easy to want to stray.  Keep reading the forum as their is much to learn.  

Instead of trying to go to a monthly allowance, offer to take a favorite on a nice trip without offering any direct cash to her. No SB will say no to a nice, all expenses paid vacation. After the trip, assuming things went well, start buying her nice gifts, paying for her books, tuition or rent while scheduling more unpaid meets. That’s how I’ve turned ppm arrangements into relationships with unlimited sex and no further mention of cash or obligation on her part.