As a contractor myself, I'll give customers (many of which are PMs) 2-3 free estimates but tend to walk when I start to get the sense that I'm spending a lot of time doing free estimates instead of actually making money.

What are some good programs for CRM, lead generation, marketing and advertising?

Also, hopefully you've been keeping bank statements to consider this an income generational property.

After 2 years, however, the property would be fully paid off and would start to generate a profit.

Is there a way that I could help him generate enough cash flow to start paying off these debts?

I don’t have a problem if you want to build a nice house; my main point is you are not getting a $400k heloc which is what your post implies.Here are my personal rules for  Building a personal residence: no more than 25% of income to payment, don’t go so custom That you can’t resell, Find out how long $500 k homes take to sell in your area; what percent of people in your area can afford it if you will sell in the future. $500 k would sit for too long in my area and I would not do more than $350k here, but that is just me.Good luck 

Service based retail that is hard to replicate online, such as convenience stores, restaurants, QSR, grocery, wireless stores, dry cleaners, medical offices, hair and nail salons, etc can generate strong risk-adjusted yield compared to apartments.

How to factor in build quality, because better-built custom properties requires less expensive maintenance on average than often-shoddy tract construction.3.

We do have over 300 hundred reviews online in various places on SoftwareAdvice, Trustspot.io, Trustpilot.com, etc which are all verified, un-moderated reviews from our customers.

From that point on that has been my quick and dirty way of evaluating.As an example, last Oct I purchased 2 4plexes that generated 5k a month in rent and purchased for $290k and put about $10k in updates into it.