My bookkeeper initially thought this was a weird setup but now has come to realize it’s super easy to keep track of income and expenses by individual property and to have instant access to a snapshot of how each property is performing.

One of the most important person on your team is your financial guy, I'm a real estate guy and I have zero interest in learning all the in's and out's of taxes, in fact I get super angry just hearing about how i'm wasting money to go into a bottomless pit of no where.

Sounds like in your situation a cash out refinance would be the better option since it is less risk and you can get a lower payment/rate verus a heloc.There is a lot of issues than can arise with a Heloc which is the same as a credit card verus liquid reserves tax free cash in hand that can be used as an asset for PITI reserves or collateral in general for compensating factors in underwriting or rate/term qualifications.I enjoy helping other BP members save more time and money I say it a lot here on the BP forum but its super helpful to avoid mistkes and lost deals as well.  

Definitely agree that there can be a super healthy relationship between Realtor & property managers, especially when they each specialize only in their area of expertise...

That right there should be reason for a super duper RED FLAG and reason for a BIG discount. 475k purchase with 100k in rehab.

If you do know them and have a good lawyer/team if something gets wonky, it's a super high demand area that will continue to grow. 

JeffCo has super onerous (and problematic) licensing rules.

Hard money or private money is great l, but unless you get a super deal, a conventional owner occupant loan is hard to beat on the first property.I’d encourage the following path:1) Lean into the sales opportunity at this job and give it your best shot to test the hypothesis that there’s real opportunity in this. 2) While you are at it, get your real estate license if you are serious about becoming a long term investor.3) Look for opportunities to get your first side sales in real estate which may synergize with this job. 

I’m also based near Philly, and while there are definitely some solid rental spots here, I’ve been curious about what other cities people are having success in, too.A few places that keep popping up in convos are:Cleveland, OH – Super affordable and great cash flow.

I am sure something like this exsists in NYS and no - you don't want to make ANY modifications to a court tested lease.We have case law in Wisconsin where landlords had to pay 6 digit numbers because their lease included what Wi law defines as 10 deadly sins - and they are not super straight forward, so even attorneys' leases got caught.