What I don’t understand is investing in something I won’t benefit from for another 34 years… Its feels like I'm choosing between investing in an income stream now (and going forward) vs. investing in an enhanced lifestyle for the last 10-20 years of my life.Any thoughts are appreciated. 

To further that mission, we've managed P&L as a portfolio (vs. individual properties), consistently investing in substantial, necessary and voluntary enhancements over decades: new sewer systems, new HVAC, improving drainage, upgrading appliances, adding new porches, etc.  

I fully intend to utilize all available resources here to continue to enhance my RE knowledge. 

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Property: Brick / Block 1570 sqrft 3/2 with additional office built in 1956 on 1 acre lot (most lots in area .5 acre or less)ARV : $185,000 (used $180000 for profit calculation to be safe)*Same house 2 doors North sold 2 months ago for $193000*Purchase Price: $90500 (seller will finance with no payments for 6 months)Holding Costs: $2000 (No mortgage payments due to seller holding note)Rehab Cost: $43000 (contractor will estimate before we sign)Selling Costs: $21000 (if I have to pay buyers closing costs)Profit: $22000The house is a time capsule with a workable floor plan.

I hope BP continues to be a place that encourages and enhances your real estate investment endeavors!

Since it is likely your purchase is legal non-conforming with respect to current building codes, any insurance needs to covers reconstruction of the structure to current codes - some policies consider code-related improvements as enhancements to the existing building.I would also closely check the co-insurance provisions, loss of rents limits ($ and time), boiler coverage and general liability caps.A good commercial insurance broker can really help assess the specific risks and you may be able to loop in your other properties under the same general liability coverage if you consolidate with one carrier.

.), generally bringing in a total of something around $2T/year as a near-term historic averageNow play with the rest of the data at will -the answers won't be mood-enhancing, but they'll sure be enlightening.PS: "THEY" ALL KNOW THIS - every single "guru" making statements without a shred of basis knows this and many other absolute facts of the current debacle and the folly of any level of taxation as its cure.the problem's quite clear, the answer is even more clear - SPENDING is the problem.

1) Finding alternative capital sources2) Creating sweat equity (buy, enhance, refi, hold)3) Negotiating tactics

Although its not complete I think pictures along with video footage of the properties will enhance to value of what I'm offering.