The neighberhood needs to look good because your ability to resale can make a difference.Good luck to you!

; do you know how that would affect my ability to write off annual expenses that occur as part of maintaining that property?

I will try to answer to the best of my limited ability.  

You want to market your property to the best of your ability.

For example, how many wholesalers in Oklahoma still use enter into contracts without the financial ability or intentions to close themselves...lots and this is technically illegal in Oklahoma.

If you do not you have no idea what they may be hiding regarding there money management abilities.

I am not sure if VA loans will allow for a cosigner but if they don't, other means of financing (FHA) will allow for a cosigner.Whomever is the cosigner will have the debt on their credit report and it will limit their financing ability. 

For example, if a plumber comes and does some work for you on December 23 and hands you a bill, but you don't pay for it until January 10, you do not get to deduct that until January because that's when you paid the bill.  

Account Closed  terrible advice... its one thing to be a bona fide buyer and another being a wholesaler trying to make middle man fee's with no real ability to close.clouding title is a bush league move.. unless you are buying it put up a ton of EM and seller is backing out then you can sue for performance... however probably not many have ever done this..

every state is different.. although in my opinion .. if your definition of wholesaling is to1. put a property under contract with minimum EM and No TRUE ability to close yourself2. advertise it with pictures etc on craiglist or other media3. get compensated for bringing the parties together then I do beleive this is the definition of selling RE that requires licensure.. it jsut depends on if your caught . each state is different on how they enforce with many only doing something if a actual complaint is filed .. other states will troll Craiglist and bust folks.