I would't consider this to be a traditional HOA as you have a fairly sizable stake, though you will probably have more restrictions than a S/MFR that you own fully.

Assuming you did a great job on the renovations, and also that you don't live somewhere that restricts doing so, I would lease/purchase the house.I'd ask for slightly-above market rent, set the purchase price at some reasonable markup from current value, and require 3-4% of the purchase price in non-refundable earnest money to be paid at lease signing.You'd get all the benefits of renting to a quality tenant and (ideally) a top-dollar sale price with no negotiation, inspection, or buyer commission!

You also get other incentives like reduced parking, and deviations from zoning such as increased FAR, building height, etc.One more thing to consider when looking for sites is to look for properties in the new Opportunity Zone, which has a lot of great tax advantages. 

If a tenant is receiving government assistance (Section 8, Abode, Vash, etc.) then they are NOT restricted to rent control. 

I need about 15-20 feet of height, and I also want something that does not grow wide - 4 feet max would be perfect.

@Daniel DietzWhen I say a Roth IRA cannot be transferred to other account types, I am referring to the restriction that it cannot be transferred to anything other than another Roth IRA.

As Account Closed mentioned the tenants being 55 plus tend to be very easy on the property.Single-family without any age restriction tends to see a little higher demand, makes sense since 100% of the market fits the bucket.

Where it connects to the house is at a normal height.

Condos do have negatives as CCRs could have rental restrictions and possible special assessments down the road. 

Also HOAs have their own restrictions.