High Maintenance Costs: Escalating maintenance costs can erode your profit margins.Change in Neighborhood Dynamics: Shifts in the neighborhood that negatively affect your property’s value are a red flag.Better Investment Opportunities: Selling might be wise if you've identified a more lucrative investment opportunity.Cash Flow Necessities: If you need liquidity, selling a property can provide a significant cash inflow.Tax Implications: Sometimes, selling can be advantageous for tax reasons, especially if you can benefit from capital gains tax laws.Personal Financial Changes: Changes in your personal financial situation may necessitate liquidating assets.Retirement Planning: Selling investment properties can be part of transitioning into retirement.Portfolio Diversification: Selling might be necessary to avoid overconcentration in real estate.Legal or Regulatory Changes: New laws or regulations can impact the attractiveness of holding onto a property.Ownership Challenges: If the burden of ownership outweighs the benefits, it may be time to sell.Real Estate Market Trends: Anticipating a downturn in the market can be a reason to sell early.Interest Rates: Rising interest rates can reduce the pool of potential buyers and lower property values.Property Value Appreciation: If your property has appreciated significantly, taking profits might be smart.Lifestyle Changes: Sometimes, personal life changes dictate a shift in investment strategies.ConclusionDeciding to sell an investment property is a complex decision influenced by market conditions, personal circumstances, and future investment goals.

Your experience in project management will definitely help you in real estate especially if you plan on doing any renovations!

Plus, with all the property, I plan to land hack and add some value (glamping anyone?

Sounds like a plan @Chrishayna Guyton! 

Please keep in mind that I plan to rent to college students and the free unit is about 2,000 sqft:- I went to transfer utilities and the past owners have a balance.

Try looking into zillow/Redfin and see what your potential rents you can get near the neighborhood by filtering the bedrooms/bathrooms of the intentional property that you are planning to buy.

The tenant should try a level billing plan and if they are qualified for any assistance. 

The city has a big improvement plan (working to bring more jobs & biotech around the health district it’s in) that’s being enacted, the neighborhood also has one that’s not yet being done.

There are a bunch of different "conventional" loans, and as it sounds like you're finding out the down payment is very different if you're planning on using it as a primary residence vs. investment.

Plan ahead if you buy in a seasonal area.