I has be rare that any tenant stayed less than a year.Other point;  NEVER take prepaid rents into the future - - to me this says the tenant him/herself is doubtful of there prospect for continued employment - - but that's just me.

You may run into a scenario where you have to pay $5K at closing for prepaid taxes/insurance and then get a $5K check several weeks/months later from your current administrator.  

Also, VA loans allow you to get up to 4% cash from seller, as long as it is applied to actual prepaid and closing costs (closing costs, appraisal, insurance premiums, etc), so if you had money allocated for this, this 4% back from seller at closing may fee up some cash for minor repairs to get past the VA inspection.

Appraisal came in lower than expected at 35k (70% LTV) and I pulled out about 22k after fees and pre-paids.

He said that in every offer he submits, he includes the phrase "The seller will pay allowable buyer's closing costs, prepaids, prorations and all lender allowable expenses."  

It really helps to know that everything is lined up, I sell prepaid legal services memberships that are one of the best deals I have ever seen.  

A close friend of mine was in the same shoes as you.Before giving the middle finger to his corporate job he paid off all his credit cards, bought pre-paid gift cards for food, restaurants, movies, and other leisure items, he got his medical and dental checkups done while he was still on insurance, and reduced recurring expenses in order to live as lean as possible in start-up mode. 

Recommend you do 6 month or 12 month contracts prepaid on the first term and then go month to month after the first term. 

Ask for a "delinquency and pre-paid" report showing all the amounts owed and paid in advance.4.

(But Im going off your quote, Im not reading through their site)OK, this kept bothering me so I dug up the disclosures from Docusign.Redfin's refund addendum says the following, so I don't see anything illegal with this.In this transaction, the Buyer would like to utilize up to $______________ of the rebateat the closing for lender allowable loan and settlement costs, pre-paids, loan discounts,interest buy-down and/or financing and closing costs.