Something else is a factor here.

Purchase price: $2,225,000 Cash invested: $350,000 Purchased a 40k sqft ft mixed use building on Main st in Middletown, CT.

What their top dollar is depends on a lot of factors and whether or not the bank pays the back taxes before the sale or after doesn't really matter. 

If you have not run your own business beyond real estate before, I strongly recommend that you get in touch with SCORE (Service Corp of Retired Executives) at www.score.org.They are a free resource (part of SBA) that will help you to evaluate the financials of the company you're looking at buying, build a business plan and to understand what you're getting into. 

I promised that we would not build a new home; the home was his parent's, he wanted it to stay What made you interested in investing in this type of deal?

Some of those building had extreme structural damage that would need to be identified by an engineer or architect. 

Another option you may not have considered is to work with a developer and build a multi-family property in a desirable area, leverage ECO construction benefits available ($5 to $15 per sq. ft.) and cost segregation and bring in a management company to manage the property once it is ready for occupancy.

These buildings are zoned like hotels and have all the requirements you need to rent and make money accordingly. 

I'll split this post into two parts based on your question...NUMBER 1: OBTAINING POSITIVE CASH FLOWIt comes down to many factors, but a few key factors that I have found that have the largest impact on the property's cash flow are below (The below generally holds true for any market.

After all PITI, utility, and services (lawncare and cleaning) costs I have $7,225.I set aside 25% of this for my maintenance fund.The remainder funds my lifestyle, wife has a Tesla, and quarterly vacations as well as business growth.In 2023 I am tracking to build 4 duplex units designed as room rentals funded in part from a recent land sale.