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!

1. plan for a 10% dip in values & run your numbers that way. 2. check out jamil damji's book on wholesaling, and use the parts about all the different ways to find good, cheap deals.3.

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

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.

Sounds like a plan @Chrishayna Guyton! 

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.

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.

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.

Plan ahead if you buy in a seasonal area.