On the opposite of the rental market there is a HIGH demand for safe, clean, and functional $800-$1900 SFRs.

University City is really big on it right now, as well as a couple of other North County townships.I would see what function is the driveway going to provide? 

Overall though, the cost on these don't seem outragous by any means and are mainly functional fixes rather than going over the top on cosmetics so at face value this seems like you should be able to comfortably move forward with it

I have had many problems with tenants clogging drains and then blaming "bad pipes" for the clog even though they were all new PVC and completely functional prior. 

The difference with a HELOC is that this product functions like a credit card with the credit balance being equal to the equity you had available to tap into. 

Get rid of the maintenance costs and it's more functional compared to a deck where boards warp, things fall through cracks, chairs can't slide, etc.

I would ensure that you are comfortable with how they intend to use the property and how many people are going to be staying and whether they intend to rotate the workers or not. 

I talked with a lender who said that this should be possible (nothing is 100%) but that doing that doesn't require positive cash flow on the property in question; it is more a function of one's general finances, appreciation on the property in question, and of course interest rates -- i.e. can you afford the new mortages.I'm curious if any of you have thoughts on whether my hopes/expectations regarding appreciation and future financing seem accurate to you all.

Your problem could be as simple as rotating the glass handle and tightening it up.

It's mostly a function of budget but Bucks is a land of opportunity - a gorgeous region with great schools, roads and opportunities for growth.