I’d love to hear from fellow self-managing landlords about the biggest lessons you’ve learned along the way—whether it’s handling difficult move outs, maintenance strategies, or unique ways to streamline day-to-day operations.

I do not know him, but the path he is leading you is a difficult path    Note difficult does not imply impossible; there are people who are successful with S8 housing    In my area s8 is so undesirable that they write laws trying to make it challenging to not allow S8 tenants.  

.- It's very difficult to argue about travel being a business expense if you're just going to look at properties, I would argue against it in a majority of cases.- Depends on what you're doing specifically, but usually I'd recommend getting an EIN at least to give access to business bank accounts- Repeating #1, if you're going to a property and 100% of your time is spent doing renovations and the like, sure, but if any of it is for personal benefit, that'd be disallowed.

You are excluding possibly the majority of available tenants to focus on the most difficult to manage and the ones who are most likely to leave your property heavily worn and damaged, all other things being equal.

I imagine refinancing option 2 would be more difficult due to the higher LTV.

First off, if you can find a property that cashflows, you're going to have a real difficult time getting the property financed.

Note: finding bank to finance deal seem to be more difficult than I was lead to believe.

to be clear - lots of other issues, lots of other challenges, and BRRRR is difficult right now with interest rates so high. 

They usually sell for a really attractive price because investment property financing is (obviously) difficult, somewhat limiting the buyer pool to owner-operator small business owners (who in turn are typically great clients, as well).  

If they are difficult, the current landlord may not give you a straight answer because they want them to find a place and move out.