Anyway, I'm deciding how to enter the game and one of the ideas I have been juggling about is how to initially replace my current salary through cash flow investment, so I could focus on rental property buy and hold investment full-time while also getting some work-life balance back in my life from my 14 - 15 hour day salaried position. 

They will get the job started much faster, they are juggling less projects (you might be his only project!)

I'm juggling this while closing on my FIRST investment property in my hometown of Cleveland, OH. 

Learning from my apprenticeship has lead me to feel capable of handling some of the labor and juggling contractors.

If I’m juggling multiple projects then of course I’d pay it.

It's a lot of work and takes a special person to be able to juggle everything.  

There's a small but active group of Rhode Islanders here who will be happy to help you with any questions you might have :)I also typically recommend people attend local RE investor groups such as RIREIG which meets monthly in Warwick and Black Diamond REI which meets monthly alternating between Worcester MA and Burlington MA.I know a lot of local investors who also work full time, and it can be a grind, but the nice thing is, banks love to see that W-2 income so it should be easier to build up (though harder to juggle everything, of course :)If you haven't already seen it, I do recommend the Bigger Pockets Ultimate Beginners Guide and of course, the entertaining & informative BP podcasts.

The first deals are slow, painfully slow, and then if you treat people right and keep consistently working, you end up with more opportunities than you can juggle without scaling up.

Given all that I am juggling, is it possible to manage a BRRRR property once I find a lender or should I rely on the VA loan even though it may not be applicable to a property that is in need of rehab?

For a family buying a new home and cant afford juggling two mortgages and keeping the house in top shape, it probably is.Another friend just got a quote.