So the average home was $100-$110k, I put down $20-22k, and 10-15 years later they are worth $420-$600k and they are paid off.

I’ll be honest it’s not clear to me real estate is necessarily a better investment than say the stock market, certainly not a bad investment but not as hyped as some people make it, you need to decide how much owning your own home is worth to you & also how long you plan to be in the area, if you will be here for the foreseeable future, bite the bullet and buy, if your not sure where you will be in a few years, renting might make more sense.

The 2-3% points in extra cost are worth it if you plan on using as I described above because the use would be for a few  months at most and due to that short term use you can survive a rate adjustment up.But, if you have no plan to payoff the debt like when using for a down payment on a long term hold why pay the extra cost for flexibility and have the additional risk of the adjustable rate with the amortization looming when you can get a fixed rate second mortgage. 

Most land bank properties, Detroit or Wayne County, are trainwrecks and cost more to rehab than they are worth - unless the market keeps improving.Be careful on the next one, but keep improving Detroit!

But the location is great, and the layout could work for a flip or a rental with multiple units.Would you take this on, or does it seem like more hassle than it’s worth?

A STR is a completely different animal in my opinion, in that it requires more work and much more compromise, but financially is worth the effort. 

Make sure you are clear on your objective so they are not showing you deals that are not worth looking at. 

Brewerytown and East Passyunk could also be worth exploring.Big projects like Bellwether can boost neighborhoods, but they often take time to show results, so don’t count on them as a main factor.

You don’t need to be someone that owns $100M worth of real estate unless that’s really your goal. 

I tried to provide constructive feedback on why it was not worth continuing with RentRedi and all the sudden I couldn't type anymore (it was about 3-4 sentences I got cut off).