That being said, I've always had a keen interest in finance and economics and I've always had my sights on someday being a landowner (like, a lot of land) and so I naturally began to look into the merits of investing in real estate. 

Then get some other evaluations and estimates.If the conditions merit remediation, use a plumber you trust to make the repairs.

However, in another property, I raised rents a lot after upgrades and did a rubs program (however in that town there re few apartments)...so there is merit to this concept but be CAREFUL and know the actual market and whats required to get those rents. 

I think they both have merit.

Any thoughts on the merits of requiring rental insurance.I’m just finishing up a rehab for a buy and hold.

@Christian Trieu The key "moving parts" in the equation are as follows: (1) the property will appreciate sufficiently after the rehab so that the second loan covers all expenses; (2) you can persuade a bank/appraiser that the appreciation merits a second loan of sufficient size; and (3) the rent you get from the rehabbed property is sufficient to cover the property expenses post-refinance.   

We approach private lenders with a package that lays out the merits of a deal, the cost to acquire, the cost to renovate (if required), the cash flow breakdown, the structure of the deal along with the Return on Investment for the investor. 

This number may be different for each investor, but every deal must be evaluated on it's own merit, and weighed against the opportunity costs (such as the return on other alternative investments, and the cost of doing nothing).

People will say, "Yeah, but you don't know what the lending environment is going to be like so you can't bank on that" - there's some merit to this, but if you can make this work now with the seller financing arrangement then you're ahead.

If humans were rational this would hold merit because most would instinctively know probabilities/risk.