I have particular strong feelings about this, but I may be the exception.The insurance and annuities side of your business will be a very distant next area of importance for me, but for a younger person that needs to provide for a young family without other assets this might be a little higher on the list for them.There is a financial planner in my local market that will also shop insurance providers (including car, home, health and rentals) to find the best value on insurance as part of their service for their clients.

I am still a bit of a newbie investor but do feel like I can add value to a project through being a licensed realtor, current business ownership experience (5 years owning an insurance brokerage), and having some capital to invest.

This is area specific, but for me it is attorney fees, transfer tax, tax adjustments (county, school and village) title fee and title insurance on the buy side.On the close side it is attorney, transfer tax, tax adjustments, and realtor fees.My latest house ($120k purchase) cost about $8500 to buy and will cost around $11-12k to sell.

Taxes/Insurance are $252/mo. 

You can always do it over the proceeding couple of days. 

A contractor is a licensed and insured business , they provide you with a written estimate and scope of work .  

Could the HELOC just be paid off, out of the proceeds of the sale?

They're more complex and costly but can be a great way to include improvements from your exchange proceeds. 

He also couldn't rent it for enough to cover his payments.So he had 1 month before the bank would start foreclosure proceedings and he was desperately trying to just break even, that's all he could hope for.When I offered to take over his payments, what do you think he said?

We proceed to schedule a court date for the hearing.