I had an empty LTR that was unfurnished and they paid an extra 650/month and also paid to furnish it for a 6 month rental. 

@Sushil IyerWith my experience, to analyze properties effectively, you can start with resources like MLS listings, Crexi/Loopnet, tax assessor websites, or paid tools like Costar and Reonomy.

I paid 20k for the first lot i bought in Charleston in the poorest neighborhood of downtown..

Specifically for taxes, its pretty straight forward with Baselane because you can tag all of your transactions with the pre defined categories for a Schedule E (the tax form you submit for rental property).

And I feel your pain.On my FLA builds my GC was very well known to me and trusted if I did not have him I would have been were you are at stalled.. but for me I just paid cash for the lots and gave no deposit to the GC ( again long standing relationship) so when he finally was ready we just funded draws on completed work .

Maybe get your debt paid down, get your first deal, get some savings built up, then reconsider the potential change. 

That isn't every family but could be worth a shot.Hope this helps and goodluck getting the HELOC paid down.

If you were able to pull out $500,000 in existing equity out of a paid off rental and disperse those funds to acquire 2, 4-unit MFR properties and had the income to support any future CapEx and the interest payments on your HELOC ( including the extra income to paydown the loan ) would there be any " gaps " or problems I'm missing in this situation where it would be a bad enough idea to not go through with acquiring more properties through a HELOC on 1 of 5 properties you own?

If he really wants to "roll up his sleeves", he can scout properties in your community (or on the internet) and get paid a "commission" if he finds one of your investor-friends in Omaha to buy it (aka, acquisition fee/finder's fee).

I finally sold it for a small fraction of what I paid for it, but I was out from under the HOA fees and taxes which at about $1,700. per year, which is a sizeable sum for me, and as we know, these fees increase every year.Bottom line is, DO NOT purchase property there for an investment.