If you provide any kind of substantial services like catering, car service, etc you will change you tax situation and no longer can file under Schedule E.

And because I'm looking for a long term finance situation, I'm not looking for a loan that is going to have a really high interest rate, with hopes of refinancing later.

Dealing with warranty service is a pain in any situation but when you also have to deal with a tenant on top its even worse.

Complicated post and I realize this might be more geared to a CPA, but figured I would try here and see if anyone else has come across a similar situation.

If a landlord plans to hold the property for a while, we always recommend an annual lease, ending to align with the summer leading lesson, or staggered with their other leases depending on the situation.  

DOM nationwide isn't really terribly useful; in extreme situations we will already know the national economic situation.

-I'm fairly careful with communication , but again, I know doing business online is way riskier, but I want to ask: Typically, I would trust someone who seems very in-depth, informative (gives statistics and numbers), and basically would give me thorough steps (including worst-case scenarios and what would best fit my situation)^^would people who have experience say that even with the above, some agents/lenders/PMs would still be sort of out to get your money and do a lousy job?

If you've been in similar situation, have you found it brings an issue down the road with future tenants or current?

We're often helping each other problem solve our listings or helping with specific situations that are occurring at our properties.

Basically they'll come up with reasons as to why the "guarantee" doesn't apply to your situation.