And if it were set up where everything went through a title company so the buyer pays the title company, they manage the buyer's loan (from me), and the title company ensures my mortgage is paid without my direct involvement... what parts of the transaction would feel risky or not worth the headache to you? 

Between the two of us, we are pretty involved in real estate.

Quote from @Kody Smith: without getting too deep into my finances, what my strategy is...1. take loans to buy properties (leverage)2. fix/flip for day to day cash flow income3. use some of the fix/flip income to buy consistent cash flow through:- business acquisition, - commercial properties (MF and store fronts),I have no intention of doing ALL of the management myself, I will hire management as needed (medium term goal)my expected core role is money provider, evaluating the numbers, making decisions, and connecting with investors, wholesalers, lenders, contractors, and property owners.while I am just on step 2 of the journey, I am looking toward step 3 to stabilize, and not worry about if house prices drop mid project or not (or not worry as much) So to be fair this is more about obtaining and growing a real estate business not simply buying rentals for cashflow.

Sometimes getting involved for a few years makes you realize you don't like it.

The requirement to do this generally involves an experienced GC signing on the borrowing entity as a 20+% owner thus making them a signatory on the loan and responsible for the debt which in most cases is not very easy to find.

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

@Martti Eckert here's the big issue that no one really talks about that you hopefully find helpful (this is copy & pasted):-----------------------------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

Add risk tolerance of the principal(s) involved, and the answer can be worked out.

This gives you financial stability during your transition.

Until there's more stability in the marketplace, the insurance market likely won't stabilize or soften either.