I'd suggest you begin by hustling your face off until you have your personal life in order and atleast 6 months of living expenses set aside.. then start putting money away to start investing. 

And the person needs to be turned in and prosecuted  LOLI am all for profit's  its how we do business.. but taking advantage of the elderly simply is not one that I subscribe too.. a 240k property that only needs 20 k in work.. is certainly NOT only worth 90k..most folks would be tickled pink to pay 150k a 240k prop that only needs 20k... had this seller simply gone to a reputable realtor and the property was exposed to the open market fair market value would have been achieved for all.Now I get Hoarder houses and super low value deals... etc etc.. especially with how intense the asbestos laws and lead paint laws have gotten.. the old days of just a wink and nob get rid of it is over.so on the face of it. some of these homes will need to go for VERY low dollars to make them viable.

So, now it's November and snow will start falling and there will be even fewer buyers in that area (the prime market to sell is April to August) so I'm facing a dilemma: do I rent the place out and start getting a steady cash flow or do I hold on until spring and hope to sell it for enough to break even or earn a little profit?

“The lawsuit is far from over so VPM is going to face far more than just their own customers. 

While doing that, I faced some hurdles around getting accurate economic, demographic, and real estate market data that didn't require a big software subscription and was also hyper local.

Meet People with Experiences Similar to Your Own: There are many organizations (both free and paid) out there that you can join such as BiggerPockets forums, local real estate meetup groups, The Entrepreneur's Organization, your local AICPA group, etc. that gives you a place to receive advice, guidance, problems and ideas.Utilize the R&D Tax Credit: Your business could receive a 10-20% refund for employee labor that’s associated with improving a product or process.Utilize Employee Retention Tax Credits: If your employees that worked for your business during the pandemic are retained through the end of 2021, your business could receive up to $9,000 each quarter that your employees were retained.Own Your Own Office: This would allow you to have multiple tax deductions, utilize depreciation, take advantage of appreciation of the property, as well as allow your company to rent out any unused space to help pay the mortgage.Take Advantage of Energy Efficient Tax Credits: There are many opportunities to take advantage of these credits such as updating the HVAC system, installing energy efficient lighting, etc.Perform a Cost Segregation Study on Your Property: This would allow your business to immediately write off the personal property within the building.Utilize Work Opportunity Tax Credits: If you hire employees from groups that typically face a barrier when it comes to employment such as people with physical or mental disabilities, veterans, etc. your small business could receive a tax credit while also helping the underserved.Use the SCORE program: This program is free and connects you with resources, and mentors and specifically focuses on helping small business owners excel.

His approach was to establish a relationship, ask where they were currently invested, provide information on investing in RE, get face to face when practical, providing more information but not a deal.

The phone conversations ive had with the office were great--as they should be, my wife and i have a fair amount in the bank with great credit and DTI--but i dont want to be blindsided with a series of unexpected questions during the face to face.

If you own the property free and clear at 40 then you'll either have to refinance at the market rate then (who knows what it will be) or face a heavier tax burden because you'll only have depreciation to write off as there wouldn't be a mortgage to generate mortgage interest.  

Others need a splash of cold water on the face, a warm cup of coffee, and then they jump in.You do you.