This would obviously reduce my cash flow on both properties, as I would be paying the minimum HELOC payment plus extra towards the principal to pay it off quickly.

Just be extra conservative with your ARV estimates and have a great team of contractors to keep rehab costs in check.

Early on in my career, I saw a close frend do something similar.. she borrowed from her circle to finance a rural fixer-upper, then paid them back once she refinanced after the rehab.I’m guessing that massive yard plus the barn is already a big selling point for your tenant, especially with a family that wants a little extra room for animals.

Going direct saves you and the seller money, giving you a lower cost to entry which helps all your numbers, but you have to put in the extra work to find that deal.

The least states:"Tenant shall pay a "late charge" not in excess of five (5%) percent of the amount in arrears for each month the arrears remain unpaid if any Rent is paid more than ten (10) days after the due date thereof, to cover the extra expense involved in handling delinquent payments.

Unless you are planning on investing in your back yard and have extra time to spend, getting a good PM is very important.  

If appreciation is slow and steady, and no extra liquidity is available, the basic fundamentals of personal finance do catch up to this investor.

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

I think the big question is how badly do you want to keep the extra $50k liquid?

Class C and D areas/properties will always cash flow better on paper, but on paper things like extra repairs, turnover, evictions and such are often not taken into account.