I know Cash is King and Cashflow is Queen, so that makes me want to go the Cash-Out refinance route, in case the market does turn and getting financing does become difficult.

., so you may find it difficult to secure an assignee if the contract is poorly drafted or your ask price is way off.1. 

From an insurance side of things, the market for senior living houses/communities is getting VERY difficult. 

Also rent collection isn't a difficult process for me; I just have them mail rent checks every month to my box # at the UPS Store, and I swing by the bank and do an ATM deposit on my way home for lunch.

However, forcing him to give you the keys could be difficult and may involve going to court.

One of the hurdles in buying these properties (and the reason you can get a good deal on them) is that oftentimes they have deficiencies that make them ineligible for government financing (FHA, VA, USDA) and make it much more difficult to obtain conventional financing. 

The remediation can be costly, and time consuming, but even after remediation, you would still have to disclosure that there was an issue, and can prove difficult to sell in the future. 

This also all assumes you can get great deals reliably, which is becoming more difficult by the day with the increase in real estate buyers. 

I’ve had a difficult time with most of the investors I come across not fitting into this category, so I am just trying to figure out where to find these kind of investors.

You always want people around who will look out for your interests.Accountant—As you acquire properties, doing your own taxes and bookkeeping will become increasingly dif- ficult.