I'd be happy to send you my STR underwriting spreadsheet if you want it. 

I say with some confidence if you keep the condo 10 years, you will be glad you kept it.  

For real estate just start analyzing as many deals as you can so you get more comfortable and confident.

Personal Liability: For claims due to Bodily Injury or Property Damage that you becomeLiable for and which is covered under the policy.

Here’s a deeper look:Legal Framework: The state likely took control due to unpaid MassHealth bills, which means there may be liens or claims on the property.

@Amir Portal  I think you should stay open to all areas. 

A HELOC offers flexibility and lower interest rates, which can be ideal if you’re looking for short-term financing with lower payments during construction.

One thing to note when getting conventional mortgages and spouses.There is a 10 limit per person for conventional financing.You can either do 10 conventional in each person's name which would be 20 mortgages for 2 people or if you do the mortgages jointly, will only allow 10 in total.My thoughts are not to own joint assets until you are both married. 

Which area did you buy your first property in? 

Probably will be Toni but you are in good hands with both.