But when I weigh the other factors- people, diversity, opportunities, WEATHER...

The independent was the cheapest but the father and son team seems to be on top of their game a little better and they have a small support staff.To summarize Maintenance1) Plumber/HVAC2) General Handy Man3) Painter/Drywall Guy4) Roofer5) Electrician6) Garage Door GuyOperations1) Banker2) Accountant3) Title Company4) Realtor - until you buy a couple of houses using one they are really not going to give you any special treatment even though they tell you they will. 

I recently got a large commercial property under contract and was told by my lender that my experience/portfolio was a factor in getting approved. 

I know it depends on many factors and I am asking you to make a very broad generalization, but in general would you think that it would be likely to get similar cash flow or CoC return in a syndication vs being able to leverage up with conventional financing in rental properties.As for HML, I have invested a fairly small sum to get a feel for it. 

Does either currently have a PM company, or would you need to find one (a major factor in an out of state investment).

There are a number of factors to consider; how long your brother has owned it, value of the property, type of building and specialty options (charging stations for electric equipment, etc.), fencing and security systems, and numerous other factors. 

Whether they are on a long-term lease or on a MTM rental agreement will also factor in.

As you know, the Pittsburgh standard treatment that tenants get here is having a thick lease thrown at them by a property manager or landlord who looks at their watch and sighs in irritation if the tenant should have the temerity to want to actually read what they're signing.

In addition, your DTI ratio will certainly be a factor at some point in your investing.

So, if our our borrower has a large arrears balance, when we do a loan mod we may factor their new rate and term on the actual UPB and defer the arrearages as a deferred balance due at the end of the term.