THE INVESTOR.That's why I say that it's the INVESTOR that CASH FLOWs the INVESTMENT... not the opposite.I think the better way to put your original question may be rephrased as "Since you the INVESTOR Cash Flows the Investment... are you confortable with a NEGATIVE Cash Flowing Scenario and what Percentage of your Investments to you have it go Negative?"

Once you feel confortable with them pay the flat fee annual  $400 and that's it.

I might have even found an investor (house flipper) that might be willing to equity partner with me given i have potentially good home under escrow. thats the thing though, i just dont feel that confortable going and talking with home owners since i am still such a beginner. so i am asking, what are the things that i should know going into and talking with a home owner?

This model is obviously not infinitely scalable , but works for now :) Insurance is not fully solved and I am not confortable with my policies right now.I have considered 3 synced listings but gone with 2 separate listings so far because my market seems to be more profitable in small units.

Even when I tried to manage the expectations and explain the differences, meaning, cleaning is once every 4 days, there's a LIMITED amount of towels, etc... but they are calling CONSTANTLY asking for favors...And in the end they argue about EVERY DETAIL (water not hot enough, room not dark enough, bed not confortable enough). 

My highest rent is 1400 for a 3 br multi level apartment.Features new hardwoodfloors and SS appliances.I spent alot (probably more than I should have) on updates to common areas such as laundry room to make overall house more confortable for my tenants so I feel that charging on the higher end for rent is justified.

I just recently closed on my first multi-family in Carolina, PR but didn't felt confortable with RE agents I met and did basically all the heavy lifting by myself (property search, visit scheduling, comparable market values, deal analysis, mortgage shopping, option contract, negotiation, insurance selection, etc.).Have you found a reliable agent?

How much rental income would you need to live confortably?

My rational for Out of State was that we currently have been grandfathered in with a below market value rent at 1500/month in a perfectly confortable place.  

If you were in Ohio, I wuld feel much more confortable guiding you.