Is there anything to suggest you would maintain it if he does not?

With some people the "pet" is poorly maintained "after-thought " !

He charges a good fee to close and "maintain" the transaction until the loan is paid off

Couldn't you set up the deal to:- give the seller thier asking price (deferred for a couple of years);- create a percentage of the rent as a seller concession to reduce the price at time of closing; and - include a non refundable deposit (say the $15K) that you get to keep.This way you are in and out and don't have to worry about buying a house, maintaining it or worrying about whether the buyer can actually close two or three years down the road.

We just do what we need to do to keep our properties maintained and keep good records of our expenses.  

I recommend that you pay that by check and write what it was for in the memo portion or have them write you an invoice.I recommend looking into a cheap copy of quickbooks so that you maintain proper records from the beginning.Have proof of what you paid.SO a copy of the ad from craigslist or your e-mail negotiating price.

Typically, you pay for it, then dedicate it to the city/county so they maintain it.

Among them:1) Depending upon your age, you can shelter approximately $49k per year compared with $5 to $6k in an IRA.2) An SD 401k will also cost several thousand dollars to open (once) but you won’t have an LLC to maintain or pay California’s $800 minimum annual franchise tax.

If you maintain any type of inventory, then you are pretty much required to use the accrual method.

Having a tenant clean, rake the yard, shovel snow off the porch, cut the grass are all things that can be implied as tenant responsibilities to maintain a clean and safe environment.