@Hector Lewis - The decision ultimately depends on your current cash reserves relative to your financial needs, as well as your willingness to reinvest for potential appreciation.

@Holly Thorsen see above for potential challenges tapping your equity in the rental.You only need 5% down for a regular mortgage, 3% down for an FHA mortgage - so why don't you have the funds?

While most of his experience is with new construction rather than remodels, he’s already given me a few pointers and is looking into potential referrals for me.

Which is very complex and costly and likely warrants professional help.Now, if it's just you and your spouse, then your 2024 tax preparation is likely relatively straightforward:- you will create a Schedule C on your personal tax return- you will NOT report any costs of purchasing the property or its rehab, not in 2024- you will report your business overhead expenses such as marketing, driving, technology etc- you will end up with a business schedule showing zero income and some expenses - not breaking the rules but potentially raising an audit flagCan you do it yourself?

I am trying to tabulate Business that may have higher depreciation but yet help me build wealth in form of real estate or potential customers for variety of services. 

I'm wondering about any potential regulations that might make this a more difficult process than I'm anticipating. 

If the seller handles the repairs, it’s usually not an issue, but you want to verfiy what your lender requires.Cleveland Heights checks a lot of your boxes (hospitals, strong tenant pool, walkability, and appreciation potential).

Thanks for the insight on where to network with potential investors, I will definitely look into that.  

Regulations & Compliance: What's the best way to research local STR laws and avoid potential regulatory issues?

The sale failed and he still owns it.One of the potential solutions is to use an SBA 504 loan for the real estate.