My overarching goal has been to accumulate enough funds to fuel my entry into the world of real estate investment.

How did you accumulate such large amount of debt?

Does it feel like the last 50 or so are sooooo slow to accumulate?

After ten years (max) those new windows aren't going to insulate any better than a single pane, and once the seal is gone it will accumulate crap. 

@Michael Richardson this will be an outside the box option to consider.Offer to sell the condo to your tenants with a wrap around mortgage on the 1st trust deed with identical terms as the mortgage and have your tenants pay your mortgage and HOA dues so you have no monthly loss.Then give the buyers (your tenants) a second trust deed/note for $100k that you carry for five years, or some agreed upon time period, with no payments that accumulates interest with the whole thing due and payable at the end of the note period.

I drove for dollars and accumulated approx. 120 vacant properties.

Just one peace of advice I’d give you before you start your journey and this isn’t to discourage you but just to realistic, after reading your post it’s seem like you have a lot going on in your life right now and a lot of financial stress, real estate is a long game but it also comes with risk & unexpected upfront costs for instance a duplex a bought which was great deal, not only required a significant down payment, but within two months of buying it, the well on the property (we had an inspection and while it was flagged as old it was supposed to last another 5 years minimum) failed not only did it fail it pumped sand into the pipes and required a repipe, was out 25k now as painful as that was I had the cash and it cash flows 1k a month has appreciated significantly & the well will last 50+ years and now it’s done, but my point is you have to have money not only to buy but stay in the game, so I’d definitely get your financial house in order & accumulate some savings before you buy.

It depends how the policies are structured and how long they've had to accumulate cash value.You want what is called an "Entity Purchase" buy-sell agreement.

I have accumulated 6 rental properties which are generating income, and done about 8 flips that sell in the 75 - 115k area, all cash.I have my sights on a larger property on Auction.com I think will go for around 120k, would cost max 80k to rehab, and would sell for 300k - This is a bit too large for my 100k cash + 6k rental income business. 

It just takes time to accumulate.