He has worked for commercial and multifamily operators that have been hugely successful by raising majority capital from LPs (syndications), but for his personal portfolio he seems to have trouble making that leap.

I wouldn't show up and cause you trouble.  

Hello everyone, I'm looking to buy my first rental property out of state but I'm having trouble picking a market.

Hello everyone, 
I'm sure most of you have heard Zillow is shutting down its home-flipping business and that Zillow is dumping its properties by selling their homes below what they paid for, hence, losing a lot of mo...

I think the best route is to test the demand in the market for a longer-term tenant and if that ends up not producing ideal results go to the STR.

I would search out the top 2 producing agents and use them. 

Hello All,
I just got the 2nd unit of my first house hack duplex ready for tenants and am using a realtor to lease the unit.
I am using a realtor to fill the unit as I have limited time and also wanted to learn from...

You might ask a title company to produce a commitment so you can see what they will require to issue a policy w/o exception for the mtg and then you'll probably need to talk with a knowledgeable PA real estate litigation attorney.

My main concern is that they might have trouble paying their rent at some point while being absent from work.Please advise.

An investment makes you money, which means you get more money coming in than going out.The trouble is, you have to count not only the hard cost to buy (price, rehab, etc... but also the soft costs to operate (insurance, utilities, etc...).