We plan to renovate it ourselves and turn it into a 1200sq ft 2/1 to STR.

You may not feel the need when you own just 1-2 properties, but it may be more relevant if you plan to expand. 

Hi JoseOverall, your plan is viable, especially with significant equity and an unconventional financing option (WLI cash value).

No, he's not an architect, he drew all designs, floor plan, site plan, etc, and we had a structural engineer design his part, and paid an architect to sign off on them.  

That’s a helpful perspective as I plan out my projects.Thanks again for sharing your insights!

Michelle Wang,With all due respect, you should make plans to be in another business once you're out of Real Estate Investing (Residential, Income Property).There are Members of our MassRealEstate dot net Association that come crying to me about similar situations as yours i.e.

We both run our own businesses but we feel that real estate will help make sure we both maintain our life plans of not needed to work as much any more.

Just a simple 499 sq ft city approved plan, single story, 1 bed/1bath/full kitchen adu with living space.

I would recommend buying a standard SFH with opportunities for an ADU, or a split floor plan where you could rent out the rooms!

I plan to do some of the work myself.