You can't convey clear title to the buyer and there is the due on sale clause that may be called by the current lender.Getting at the $130-150K of equity will be challenging without selling the property outright.

If the lights stay green, you'll need to engage at a minimum, civil and structural engineers.  

I love going to different homes, seeing the vast differences in quality and layout, comparing them to the local market, and putting it all together to make a "big picture".My largest challenge so far is developing an effective marketing system. 

You are choosing the road less traveled and there are challenges as a result.

For which Midwest cities do you want to do this challenge for?

Now thinking on buying the next one, but it might be challenging due to low on funds, it might take awhile.

The tenant likely has the right to stay in the property at the rate on the lease until the lease expires, but all rents should now come to you instead of the HOA.More than likely, the HOA lien remains in place and you are now liable for it.The receivership company that the HOA has engaged with (the HOA can't manage the property directly, usually) is likely very expensive, so you'll have to work to get them out of the picture.I'm the president of an HOA that has a unit like what you're describing.  

Will they engage with me at this stage in the pre-purchasing process?

Might be challenging but possible.History:I bought the house I currently live in back in August 2017.

The other half the time, the engage and work me as a lead source.