Start with small steps, keep track of what you do, and regularly check and tweak your plans.

Is it different then regular insurance?

Most homes in Milwaukee sell with multiple offers, so instead of more contingencies or tests we currently see about 56% of all offers without even a regular home inspection.

If this is Hamilton Couty, there are three or four lawyers who have regular dockets in the Eviction room.

Might be worth chatting with the great folks at Dirtfish if they would be willing to promote your vacation rental or even package it, they have wealthy clients coming from out of town regularly, and the local hotels are very expensive....any vacation rentals close by would probably make excellent options.

There are several skip tracing providers but oftentimes they use a database that isn't regularly updated.

Think about your down payment, which is often 3-5% of the home's price for regular loans and 3.5% for FHA loans.

I recommend you do same quick exercise with the real numbers and determine if the profit justifies the risk and effort.  

I’ve never made more than $50K from my W-2 and the highest paid year was during Covid when I got a bunch of bonuses for being a healthcare worker so was not indicative of my regular salary.

I sent same letters regular mail the next week.