You need to live within 50 miles of a unoccupied STR, you need to be living there, lottery system for new permits and you don't get one, STRs are banned overall in certain zones, HOA votes to disallow STRs.

Traditionally a mentor is not a paid position and good investors  dont sell good leads. 

Traditional banks with Fannie / Freddie / conventional loan types will sometimes push back on the LLC issue, but there is a BIG world of funding and lending for investors outside of that box.  

I don't flip, but from my understanding you would not use a traditional bank to get these loans unless your rehab is over 6 months, you would use a Hard Money Lender.For long term buy and hold I would leverage the duplex and buy more properties, and then I would use the profit from wholesaling and flipping to buy more properties.  

@Chuck Wiggins I've heard of rental loss insurance for property damage, but not for rent (unless of a traditional insurance claim).  

If I was renting to traditional private pay tenants Germantown might not be my area of focus.

We know it makes for a slow start, but we don't have the traditional 20% down nor the reserves to take on reno.

Normally I don't socialize with my tenants but they were paid up for the next 6 months so I decided to take him up on it.We had such a good time we decided to make a weekly tradition of going out for wings and by the end of the lease we had become such good friends not only did we get wings weekly but they also invited me to go on vacation with them and they invited me to be a part of their wedding at an inclusive resort.They only rented from me for 14 months and they got a heck of a deal but they are now lifelong friends.

Once I grasp the different traditional forms of financing then and only then can I become creative without worrying about going to jail, getting a divorce, or those other horrible things you mentioned. :) Thanks for the brute honesty.

It's hard to find a fund that isn't a REIT to get involved on a larger scale unless you are able to put the downpayment on a piece of property there, Traditionally only the large hedge funds and pensions that have been involved in this extremely unsexy (yet, cash flow liquid!)