I currently have a pre-tax retirement account with employer match and a Roth IRA invested in the stock market.

In digging into the details through public record searches I find out that he has had 3 evictions, several drug convictions, and a violent crime.

If you had a couple million in equities and a need to diversify your holdings by adding real estate, maybe.

I believe these systems only work if you have good employees, in which case a bonus is unnecessary.I provide strong compensation, some benefits like 401k, growth opportunities, and a strong work culture.

It sounds like you've absorbed a bunch of problems already and a new sewer line and the current basement situation will cost you way less than the $50K in fees to sell it. 

Last year was back to earth; a glut of available properties drove the rates down for everyone and a drop in visitors also increased vacancies.

Also, if the LazyDog exits at some point, and a new tenant needs to come in - who will bear the architectural/remodelling expenses?

I Joined Jeromes Buying land and building homes program back in 2019Heres my opinion on my experience....First and foremost He offers two different programs. a 6 month program and a 12 month program.BOTH PROGRAMS ARE EXACTLY IDENTICAL THE ONLY DIFFERENCE IS:You can choose to have the weekly mentoring by Jerome once a week for 6 months or 12 months on a zoom call and you can have access to a private networking group of real estate professionals whether that be (realtors, contractors, brokers, Private/Hard money lenders, loaning institutions, Surveyors, Engineers, Zoning Board members in different municipalities, pretty much anyone you would need to get a project completed) for either 6 months or 12 months.6 month program will run you $5,997 if you decide to pay all at onceor you can make a $2,300 payment every 2 months totaling $6,90012 month program will run you $9,997 if you decide to pay all at onceor you can make a $3,000 payment every 3 months totaling $12,000I decided to join the one year program and chose the payment option as i figured within 6-8 months i would have my 1st project completed therefor my last two payments would essentially be covered by the return on investment from that project.PROS:The group is really a family oriented space where you meet a vast variety of people from all types of background throughout the country and other countries that are doing business just like you.

That’s why you get a discounted interest rate and a lower downpayment, because owne occupant properties are low risk. 

Plan to buy at 4 duplex and a single family(which includes a lot) this year.