It sounds like the peace of mind will make the time & cost worth it for you (in addition to higher resale value).You can hire Suite Additions (or similar businesses in Hamilton) to come and assess your property’s requirements for a duplex conversion, and then choose to do the work yourself, or have Suite Additions do it all for you.

I was thinking about trying to reach out to the owner, but after seeing the mortgage companies name on the tax assessment I am wondering if that is even an option anymore?

Your tax rate will be approximately 3% of the property’s assessed valued.

@Talen C Honeck Nope, the code violations (which can generally be negotiated way down) and the HOA past dues, not negotiable, should be the only things hard to assess.

Some times, they will force a special assessment, can be several 1000's of dollars per unit if they are short in reserves, for necessary CAPEX or repairs. 

I picked my own inspector just to make sure the assessment wouldn’t be biased, and I attended the inspection in person.

I just found out that there will be a special assessment in the near future on the condo association.

The net profit is the difference between the assessed values at purchase and sale, taking into account any miscellaneous contributions over the course of ownership.Then, you'll have to pay the US capital gains tax, against which you can credit the tax paid in Mexico.

Live at home and have your mom make your meals.Do that for a couple of years and then re-assess your situation (and the economy at that time).Get a second job doing something that pays well and save 100% of that.Cash is King!

Go back to the drawing board, assess YOUR life and YOUR goals, and if the Misses is not a good fit, well, you know the answer.