The only thing I'd add would be to say that once you get your markets narrowed down, pull the trigger on the team you like (more than the market).

Wanting to keep current townhouse and transition it into a rental unit and looking for some help with that process...Unsure on the timeline of this occurring but wanted to get prepared as best as possible to pull the trigger if a good house in area I'm looking becomes available to purchase.

This likely would be considered a change in ownership triggering a property tax reassessment and that could amount to big dollars depending on when your mother in law bought the house. 

Everyone always says "if the numbers make sense" but people come up with a million and one reason why to not pull the trigger when the time comes.

Price - reduce the price to your absolute minimum - it would need to be 30% below market to move quickly but this will trigger buyer fear so counteract that by..3.

I would caution anyone from being a serial HELOC user though... theoretically a bank can call that loan whenever, and although that is extremely rare, extremely economic turbulence could be a trigger. 

You could also establish the time period to your liking and have it triggered only below a minimum balance.

Have followed along at a distance for a while and just pulled the trigger on pro today made the decision to move full steam ahead with this side hustle. 

Consuming content generally gives me tons of information that I still have to sort and massage to try and apply it to my situation. 

You need people that are going to pull thee trigger.