Others might be fine with taking risk, but least by doing this a person can get an idea of what might go wrong. e) Legal document analysis: it will usually take a few days to go through the legal document properly, as almost inevitably there are tons of gotchas that either have to be explained, or mitigated with a side letter.

@Edward Liu - Section 1(e) of the Contract you linked to states:In the event of a breach of this Contract by Seller, the Earnest Money Deposit shall be refunded to Buyer, upon Buyer's request, but such return shall not affect any other remedies available to Buyer for such breach.Failing to close is a breach by Buyer.

I am currently renting a place in a good neighborhood, and wanting to buy it from the owner, I e-mailed the property manager to ask the owner if he/she will be willing to sell it to me.

It provides cash flow that I live on as I self-manage my commercial/residential r/e rental portfolio which is a longer term play. 

@Derrick E.

@Carolina E. thank you!

@Sharon S.I use google drive for storage and cozy for rent payment and beaver for accounting/bookkeeping and schedule e preparation. 

@Chris Politylo  In general I believe most STR owners go the traditional financing route to which they are usually going to have to show previous schedule E/C tax returns to prove monthly revenue to apply as additional income when qualifying.  

@Josh E. you should involve your contractor from the beginning prior to making an offer so you know what needs to be done and how much it will cost.

For your rental income part they will usually take your average of the last two schedule e tax returns and add back the depreciation expense.