I use the TX bookkeeper @Chris Seveney is referring to for my main entity, but I use WaveApps for all my other entities, and they have a free plan, and also a wizard that can help you set up your chart of accounts. 

Acquiring the 2 additional properties is mainly to get to a cash flow goal where I could replace my W2 income and go into real estate full time.

I've been speaking to landlords recently and one of the main topics of conversation is "I want my rental rate to cover my mortgage."

Mattress, main couch, sheets, hot tub?

I haven't bought a deal or anything I'm still saving up, I'm at 25k I'll hopefully be ready to buy in the next three years, otherwise the city I'm buying in is Barrie which is generally a great appreciation market, I've got two brothers Chris owns two rental properties and Ryan just bought his first partnering up with my brother chrises second deal, so I might partner up for my first deal I don't know yet tho depends on what my brothers want to do.when shopping properties I do remember from the book you shouldn't buy properties based off cap rates but im wondering at the beginning do you first skim this information say the property is listed at a 6% cap rates which is common in the Barrie market would I then would go walk the property and see if things are viably ok, once I believe it's resdy for a professional inspection I'll get information about deferred maintenances mainly capex based off what I need to repier I'll be walking the property with the professional and I guess he'll give me a rough cost of How much everything that is needed and when I need to get the work done due dates, also I don't know how to calculate how much I should set aside in monthly terms after I get the required information from the inspector I'll be doing this for the first time, if the pure cash flow is incheck  I believe usually NOI is usually around 60% including appreciation and mortgage income andone going deferred maintenances around 35-40%, now I'm ready to make an offer?

But for the second one being able to visit will make things easier especially during contracting time. my first airbnb, I wasn't around and construction took a while which left me with the feeling that I should be monitoring and visiting the location more frequently. additionally, my main goal is covering my w2 taxes via the short term rental loophole.

Maine in particular has a few markets with a decent amount of multifamilies.

Then the website for the PM company crashed just as my property was to be listed for rent and their main point of contact left town.

The main problem is that most customers just look at the bottom line and mortgage loan officers know that. 

This side of town is mainly B to A- neighborhood.