Readers should seek professional advice.

I have other HELOCs that were much easier to get both personally and professionally.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

The idea is to convert a multi-family building into condos; but not in the traditional sense where you separate pre-existing apartments into their own condos; but in a way where you combine the common areas of all of the apartments in that whole building, and turn the individual rooms within those apartments into condos themselves; thus transforming the hallways, kitchens, bathrooms, living rooms, dining rooms, porches, balconies into common areas of the condos. 

Readers should seek professional advice.

We are not real estate professionals.1) How would you handle the classification of the property in the 2023 tax year and would you utilize a STR depreciation strategy?

Curb appeal for higher-end properties will be much more important, especially when it comes to marketing - most ads and main listing photos feature the front of the property.In this case, I would consult with a professional - i.e. landscape designer or stager.

Sometimes condos/townhomes are better at attracting young working professionals given that they are usually in more densely populated areas and often will have amenities that come with the HOA like pools, gyms, etc. 

You have acquired skills that are worth 500k, so maybe you can translate that into an adjacent career path and leverage your existing skills?

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