I am about to rent out my single family home that I personally own.

This is just one persons opinion coming from my personal experience: The challenge I'd like to leave for anyone who wants to break your golden handcuffs of a 9 to 5: If you want a different outcome, you have to put in different inputs.

What are some tips you used to find your favorite handy person?

The person moving out also have the option to find a replacement. 

I personally own 12-doors in Detroit proper and I'm happy to send folks resources about the market there and/or chat about my experience.

The following link might have good info, but it's from the standpoint of the person who owes the IRS.https://www.irs.gov/payments/offer-in-compromise

Personally I don’t know if I’d take only a $50k downpayment on a $350k home if I’m using a realtor.

You sound more suited for a high yield money market account or CD.

Be careful where spending your money over there.

Quote from @Michael Plaks:3 weeks is a super short time.If I don’t want to rush, can I still file/pay my 2023 taxes as is and then amend the return over the next few weeks to get money back?