My advise is to start with single family or a small multi-family ground up project first but this market environment is truthfully not the time to be completing any ground up projects unless you are self performing the construction which it doesn't appear you are in a position to do.There was a recent Philadelphia  forum chain started by someone else who was contemplating ground up in a similar fashion to what you are proposing and I cautioned they would be better off buying something that was newly built and believe after conducting their own diligence realized it was too cost prohibitive at this time to build with 3rd party GC's in Philadelphia when also accounting for the interest rate environment and cost to build.

And as far as the relationship advise, is that kinda like saying "hey you know your girlfriend kinda looks fat in that dress, you should probably tell her that" or something along those lines? 

Any help, advise or recommendation would be greatly appreciated. 

@Shahaf MatityahuYou apparently checked with City Planning which zoning is part of, and they advised you it's for only 2 apartments.

There are still superb oportunities, but if you come and buy without advise, it could end to a disaster. 

I can't advise you how to mange STRs but I have had to deal with BBs many times in our apartments.Finding whether or not you have bed bugs is pretty easy. 

but you also want to create an incentive for people to stay.From a tenant's perspective, there is also a monetary cost to moving, not to mention the effort it takes all the way down to the little annoying things like  changing the zip codes on your credit cards or address on your drivers license.Great original post by the way, every new investor should read it. 

You can use generic estimates for each of these expenses (which is advisable), but then readjust those estimates for any specific property you are looking at (seriously).

We never advise breaking local regulations but we have managed some that were not zoned for STR, and did not have a problem until recently. 

Any advise would be great!