I know can't predict the future etc. or bet on depreciation, but it seems like I'd be buying into a high point in the market which of course is never good. 

I did take offense at that and I don’t understand your offense at my calling your and my plan common sense.I don’t know much about you or your finances but I’m still betting if you had stuck with your first option your dreams would have died at about 3 properties.

What are some of my options or is waiting it out rather than spend any more money on legal the best bet ? 

Your best bet is to visit this and learn.

And I bet they have to stay in touch on their vacation.   

@Jeff S.Of the 5 you have listed, I would say 4 and 5 are a better bet on getting cost.Don't quote me on this but...I've had a few appraisals/inspections from my previous buys and can't honestly remember if I saw in one of those documents (maybe the inspection) where it was indicated the remaining life of say HVAC.With that said, you can always take a picture of the system (HVAC, W/H) serial# to get the year it was manufactured.

I would bet that the other markets are the same.

I guess your best bet is to list it for rental and hope you get a decent cashflow but with those numbers I see it difficult.

Then, I imagine I'll pull out the equity of the investment property to pay off and free up the HELOC funds.That's one way to go, but you would have to wait/bet on appreciation of the investment property in order to do that.

I'll bet as you get better at analyzing rehab costs and risks you'll start finding more efficiently.