There’s not a whole lot of background information in your post (financial situation?

VERY... that's why hard money totally dominates the lending landscape in fix and flip in our market. or cash.

Background:5 years ago my wife and I bought our starter home. 3 bed./2,5 bath w in-law apartment, 2200 squ/ft in New England.

It really depends on your background and/or who you have working with you. 

@Jacob BassettNo single answer to thatStart by reading this https://www.biggerpockets.com/real-estate-investin...You need to decide for yourself based on your own skills, background, network and capital as to what is best for you in your market. 

Note: I am aware of online applications like cozy that makes sure they fill out and pay their background/credit check but the applications for those types of software doesn't cover everything I want to ask and Brandon suggested paper applications is the way to go so it being my first rental I'll follow his advice on that but I just need a robust way of doing it.3.

I had a back ground in dealing with "people" and went in with eyes wide open.

Greg:    First, do not get discouraged by anyone, someone else is doing it so you can, not going to be easy.If not done already I suggest to look into this:Enforce that PM uses a great website for rental screening, ones with a background check and choose the best tenants possible.Review you leases to close any pitfalls and enforce the lease to the T.Keep the units in good shape and keep extra cash reserves ( fixing + trip expenses )Tiger than normal lookup on the PM ( have second PM line up ), vacancies, unit showing costs, repairs, fees, etc,  require a once a week normal operations report and a once a month full operations report.Family, friend on virtual assistant that regularly drive by the property and reports to you, or if cash flow allows and deem beneficial you can install security cameras and remote view activity on the property, nowadays there are lots of options.Check if feasible to get a home warranty plan for the units so some pain issues are self-managed by the tenant via a phone call to the warranting companyIn which city/state is the property? 

This makes me doubt all the criminal background screening that comes back as clean as well.I believe that the issue with Maine is that our court data isn't readily accessible online. 

POL came on the scene and they were doing HML at very high rates and points in NJ .. so my back ground other than recreational private aviation that I pay through the nose for.. :)  is HML  and I am thinking wow .. this is going to some heartache and sure enough some of the folks that posted have done like 10 loans and 7 are in default.. the foreclosure time in NJ and NY two states I personally would never be a lender in is 2 to 3 years.. and by the time you get the asset back its ouch time.. and that has played out for some folks and there is a high profile one in Atlanta that has been going on for years.. suppose to sell at 6.5 million and its listed under 3 now.. although I think they may get their principal back or most of it but its been 2 or 3 years.. and you know how investors get stressed.. and then the other issue I saw coming with crowd funding .. and remember my background is I have owned 2  Hml companies over the years one of them in Oakland CA with 250 clients and about 50 million under management.. these guys went about raising money from 5 to 10k investors and would literally have 20 or 30 investors in one loan..