I would recommend keeping it on if you plan to move into it (ideally immediately so you can keep the prop tax discount)  or if it has sentimental value.  

Ideally, I want more booking through Furnished Finder (to cut down on AirBnb fees), as well as direct from insurance providers, relocation specialists, etc.

Ideally these tenants are also in unrenovated units, so you get the unit back to renovate and a trouble tenant out.  

Ideally, rates will be a bit lower and will help psychologically.

I will ideally find a home that doesn't require a loan and if I need to put an additional $100k I can with cash I have on hand.

Ideally short or long term rentals.

Hi @Rita SamaddarI recommend areas based on three things:Budget: Knowing your cash to close helps me suggest the best areas, especially if you're using a hard money loan.Rehab Level: Whether you prefer low or major rehab impacts the neighborhoods I'll recommend.Market Dynamics: Areas with minimal days on market are ideal, as they predict how quickly your property will sell post-rehab.In conclusion, start with how much you have to work with and the level of rehab you're comfortable with to find the best areas for fix and flip.

This can be straightforward but may not be ideal if market conditions are unfavorable or if there are significant transaction costs.Partitioning the Assets: If there are multiple properties, you could divide them between yourselves in a manner that reflects the 50/50 ownership.

The Challenge membership might be ideal for you. 

Once the DADU is finished, you can refinance your property, ideally through a cash-out refinance, to pay off both the HELOC and the construction loan.