Tuck point work as been done on a yearly basis and will continue to be done.

Would you try to rent the condo out or would you continue living there?

Also, if the tenants end up staying, I would educate them about not doing any repairs on their own anymore, and to contact you immediately with any problems.

You're on the correct site to begin your educational journey.

I also recommend reading Brandon Turner's book (buying rental properties with no and low money down), and just continue to save as much as possible. 

People get excited about the 'guaranteed rent' from Section 8 programs, but they don't realize that tenants can lose their voucher, there is a maximum amount the program will pay based on the Fair Market Rent for your area, and that you must have a yearly inspection, even if no tenant turnover has occurred, and that it's very common to fail these inspections, meaning you have to fix things and then be reinspected in order to continue to qualify. 

I shall continue to search.

As far as the issue you might have where you may be using language in a contingency in your contract but where the contract continues regardless what happens, you need to review that with council then because that isn't really a "contingency". 

Boston continues to grow and add lots of housing.  

@Reese Barker Educate yourself first on the various options, then decide on your niche, and only after that take the next step and start investing.