As the PM you are stuck between the owner and the tenant and both have conflicting ideas on how money should be spent (or not spent).

I had to change insurance companies, raise the rent and I used a company called Ownwell to help reduce my property tax.

This will at least minimize your tax bill.

I do have an empty lot next to my current SFH , doing nothing (but costing me money to mow :)) my thought was to build a detached guest cottage to serve as an overflow for guests or it could also serve as a seasonal / monthly rental.

if the building cashflows really well ... it wouldn't be a big deal to use a loan for dp right...at 10% down for lower income housing I don't have much money and I think that this is the best way to get multi-family management experience to meet hud loan requirements in the future which Have the lowest Down payment options.Am I overthinking it?

Keep exploring and stay persistent—there are opportunities out there that can help you expand your portfolio.Remember to incorporate tax savings into your strategy.

Investment Info:Large multi-family (5+ units) hard money loan investment in Johnstown.

I've taken all the major options to consideration such as book keeping, accounting, taxes, payments, maintenance/trouble calls, price of software etc.At this point, I'm looking for the most balanced option that will best help protect myself and my assets.

On large liens, ($15k +) where there is a risk of tying up money and budget for a long time is a risk, we usually do a quick bankruptcy search.

I've have read many books, listened to many podcasts, and read many posts on this forum and still do so, but I sat on the sidelines for a number of years just trying to save enough money in my emergency fund before starting to save some down payment money.