3) What neighborhoods would you recommend in this price range if I'm targeting high quality tenants?

Those qualities can be the difference between closing a deal and walking away empty-handed.What about you?

You lose because there are many other suckers out there falling for the same line and sharing the same low-quality leads that don't translate into sales.Do the math.

Contractors, unless you have a working relationship with them, normally do not want you bouncing ideas off them.Understand what their hourly rate is, have a discussion with them that you are okay with paying them an hourly rate if they walk the property with you and provide you a scope of work along with an explanation of what you can/can't get away with in regards to improvements.ask them if you go with them, if they can credit you the amount that you paid.Once you develop a working relationship with a few contractors, you can bounce ideas off them and expect quality responses.I do not invest in New York.Best of luck. 

DOM can be minimized by a number of different factors including the quality of marketing, rent price, availability to show. 

The mailers I receive for my properties are not of a high enough quality, to make me believe the sender understands what gets a recipient to even open or read the mailer, let alone respond. 

Given your previous career, your goals, and wanting to diversify your investments, I'm wondering if you might find value in the PassivePockets community, it's a community with private forum dedicated to passive investing in syndications.

@Christopher HeidrichRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

I’ve never actually been legally owed money before so I was green on how to handle things while trying to be understanding and respecting other lifestyles and career choices.

The license doesn't cost more, the service and quality does.And a note on that cost, in my experience hiring contractors, only a small percentage of the cost savings was due to finding the right guy who is willing to work for less.