You might find a contractor to do the work after you have a buyer and have the roof done and paint the house after contract and before settlement, you can pay the contractor from settlement.If the seller won't go there, you may take your option and buy Sub-To, then contract with your buyer, contract for the work to be done, upon completion go to settlement and again pay the contractor.A buyer obtaining a mortgage: The appraiser will note the deficiencies to be repaired, work can be done and the appraiser will do a final inspection so you'd work that into the Sub-To mentioned.Lastly, a buyer can agree to buy and pay for repairs needed for the lender, still accomplished as mentioned, paid upon completion of work or through settlement.

When I went full time in my business, being a finance type, I did the same thing all the other finance types do starting off, attempt to quantify the value of RE and investments, including notes.

Obviously the lease would have to be gone over with a fine toothed comb to know exactly where you stand.

I am looking to learn about opportunities in the industry for a finance major with little of his own capital.

In fact my assistant sends me a final accounting on every single deal with the total profit made, the total overall return on money invested into the deal, our personal return etc, and I have a spreadsheet which shows how we are doing as well.

Otherwise, most larger suburbs have pretty strict ordinances that prohibit "bandit signs", so you can expect code enforcement to get them eventually, and that could come with a fine.  

My goal is to work for a Big 4 firm and eventually work my way into a finance department at a Fortune 500 company.

If the hoarder is the tenant, it's best to make the contract contingent on the property being vacant with a final walk-thru before closing.

That was a fine strategy a couple years ago when half the properties listed on the MLS would make good flips, but these days, you're not going to find a lot of great deals on the MLS -- whether in MA or CT. 

I have a finance degree, but I only use what I learned from a couple classes regularly (getting to NPV from a future income stream).