I know NJ is tough to evict, and maybe this wasn't unreasonable (it's the reason I'm not investing in NJ anymore).

So yes I thought with such early notice and you're still getting rent for April, May and June on a lease which expires July 19th was not an unreasonable request. 

Jake,It sounds like the limiting factor on your file will be a combination of debt to income (dti) ratio and loan to value (ltv).There are many lenders out there but the majority of them have underwriting overlays that create more hurdles for borrowers to jump through.You and every other investor needs to work with a lender that only underwrites to Fannie Mae, Freddie Mac, and Ginnie Mae's base underwriting guidelines.All of that being said, for a conventional mortgage, Fannie and Freddie are currently limiting the maximum LTV to 80% for a cash out refinance on a single family home. 

Not saying it is impossible, but you should have a pretty dialed-in plan and approach to overcome the age barrier, which any homeowner will instantly recognize and throw up as your biggest hurdle.

Can someone provide insight into how they got past these hurdles?

I think $40k closing costs is unreasonable for a $1M purchase for NYS.

LandlordIs there a part of your business that is a consistent hurdle?

Unless you are on the board, you won't have much control over unreasonable special assessments, HOA due increases, new laws about no rentals, and restrictions on what you can and can't do to your property, how many people can live there, etc. 

For me, I think the biggest hurdle is finding property managers to manage any properties that I find.I have been listening to the Bigger Pockets podcasts and I am very encouraged by all of the offers of help.

Are there additional hurdles today that have to be overcome...