I managed a single rental during my medical residency and even that was a headache at times.

I don't really understand what you mean....The best "tweak" I know for a primary residence is to use a FHA 203k loan. 

I have a primary residence that may be a cash out refinance candidate. 

For me it's kinda worth it because I'd clear about $1,800 a month once all the units are occupied with paying residents.

Why do you plan on owner financing when you could get a Conv or FHA loan for a primary residence with 3% or 3.5% down? 

I wonder if there is a service one could subscribe to or access which shows:- Total value of residential mortgage debt in the US- How that debt is grouped by fixed vs ARM rates- How thar debt cuts in terms of prime vs subprime- How are the monthly payments doing (on time vs late)- Proportion of foreclosures (growing or declining) - How much of the debt is primary residence vs investment - Average loan to value estimate My point is simple.

However, I have to get a loan for a primary residence later this year so switching to a 1099 position now doesn’t make sense.

One time when I was looking for a primary residence an agent set up some type of account for me to search and access the MLS.

I'm in the process of planning out the build for a property management lead generation CRM and want to get a general idea about how different investors setup the lead generation flows and what information you consider important to help you convert a new lead into a paying resident. 

On Fridays at 6, we have a resident HOA attorney on drinking schedule until 9 that'd I'd love to introduce you to, as well as sporadic visits from some great members in the insurance industry.