This is just off the top of my mind when I think about Tenant Representation and Landlord Representation issues that arise when one party submits a Letter of Intent.

The issues typically arise out of "add ons" after a totally fine K&T wiring was initially installed way back when: people add, typically in a haphazard way, modern wiring to the old K&T wiring, possibly even messing up the breaker system by adding higher amps circuit breakers etc.

I know some investors will clearly accept the risk and not get a survey but every once in a while this very issue arises to bite them in the back side and a survey may have been advisable.

However, if your properties are cash flowing, then a rise in cap rates after you buy will not affect you.  

As well as enough property to add an equal size home, or some combination, should the need arise.

Buy the home warranty for the peace of mind (if the peace of mind is needed) and as you get more comfortable, you can change the way you insure the protection of your investments - "fully insured" (e.g. home warranties) or "self insured" (e.g. pay for situations out of your capital reserves as they arise).

Maintaining the "Prohibition of any illegal activity" clause will help the landlords case should a problem arise with the Feds.

They tend to allow tenants more leniency (not always) and issues can arise.

When presented with all of the scenarios that could arise it definitely makes more sense to pay him as a contractor, and possibly discuss a partnership when we both have skin to put in the game.

I have a lawyer be the trustee for our land trusts, if a situation does arise and it does go to court, I do not want my interest disclosed.