After college I worked as a construction estimator for a high-rise developer in Toronto, and currently VP of a civil general contractor in Sarnia, ON.We cashed out of the city life a number of years ago and split the proceeds to by our own home and our first rental property. 

Success is being able to spend your life in your own way.

I've decided to transition out of the 9-5 cubicle life and begin investing in real estate again, SFH and multi is what i'm mostly interested in.  

How much is owed on the 1st, how much is owed to the HOA, and how much is the home worth in it's current condition?

It may have an affect on whether or not they accept the offer but your numbers should strictly be based on the value of the property in its current condition and market.  

In the current condition, the property may be worth $50-$75K.

If this house were in perfect condition: with new flooring, paint, landscaping, appliances, fixtures, it would sell for between 400-420K. 

You can have multiple FHA backed loans, however you must always live up to the conditions of the loan. 

And that takes tactfulness (which I'm still working on) when communicating with your partner and mutual respect.Lastly, I'll leave you with one practical thing that works really well for me and my wife (In business and everyday life).

Retail from $4-8k in good condition.