- repeat issues: we pay for the first drain unclogging, but if it was because of something they put down, they pay for the second and we will let them know at the first time.

What you are looking for, based on your list, isn't out of line. 

After 6 months you'll know what strategy you want to deploy, and have the confidence and knowledge to do it.This can also provide time to pay off any consumer debt, save an emergency fund, and start saving for a property as needed.

Plus, you may qualify for bonus depreciation on improvements like HVAC or plumbing.Owning the land matters: If you own both the home and land, you gain equity, control, and more depreciation opportunities (e.g., fences, driveways, utilities).

Quote from @Connor Chanter: I have a couple rentals near Milwaukee, I'm looking to do a cost segregation study to accelerate depreciation and recapture some bonus depreciation from the last few years.

As I was living out of the country, I set up 'auto-pay' for regular bills, and alerts on bank accounts to keep abreast of any excessive dips in balances or unusual activity in general.

It's already a known challenge with sunk costs.So, pay close attention to your monthly statements and, assuming you have a PMC, chat with them at least monthly for 30-45 minutes to learn more about how they are managing your property.BTW - w/o you doing more research than you did before buying these two properties, STR will just be the next "shiny object" you gamble your money on!

Is it common for there to be a discrepancy between what section 8 is paying and what market rent is? 

Bigger Pockets is a great place to find an accountant specializing in real estate taxation.A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation, 1031 exchanges and tax planning.I recommend finding an accountant specializing in real estate taxation, business taxation, financial planning and tax planning.Consider working with your accountant remotely to expand your options.I would also recommend looking for an accountant willing to work with you throughout the year.

As I was living out of the country, I set up 'auto-pay' for regular bills, and alerts on bank accounts to keep abreast of any excessive dips in balances or unusual activity in general.