I would suggest using this website to get a general idea of the locations you are interested in. https://www.areavibes.com/Its pretty cool because they give you a total livability score and you can just see the different data that they give you

For Property 1: Should I sell this property and transfer the equity into another investment, or should I explore ways to lower the monthly payment and break even or slightly positive on cash flow?

@Delmar Marsh JrAs you begin your investing career I would suggest using this website to get a general idea of the area you are looking to invest in. https://www.areavibes.com/Its a great starting point and gives you a whole list of data that you can look through. 

You can type in the properties address and it pulls data from airbnb and other short term site to give you from what I've read a pretty accurate estimation of Occupancy rates and income.

The most recent data show that record momentum continues for the residential rental industry especially for the short-term rental industry, with year-over-year bookings now exceeding pre-pandemic levels.The complexity of the problem hinges on the definitions of “short-term” versus “long-term” rentals for tax purposes.

I've been managing places for my aunt up here and in SoCal for about a year now and personally believe that how often a tenant asks for fixes is more based around their personality than anything else.Take my opinion with a grain of salt as I've never used a PM service so don't have any data to actually compare.

Your problem is likely in the data you relied on for your expected return and their experience.

Heres the numbers:  Borrower(s)Subject PropertyRate Not Locked 9/30/2024 Sales PriceDown PaymentLoan Amount30 Year FixedContract DepositSeller ConcessionNMLS#  $670,000.00$167,500.00$502,500.007.000% $0.00$0.00  Bank Origination Charges Estimated Title / County / State ChargesOrigination Points % $ - Owner's Title Insurance $ 4,415.00Discount Points % 1.500% $ 7,537.50 Lender's Title Insurance $ - Underwriting Fee Title Search $ - Appraisal Fee $ 650.00 Title Services $ - Credit Report Services (1) $ 299.00 Alta 8.1 $ - MERS Fee $ 25.00 Recording & Transfer $ - Flood Certification $ 8.00 Notary $ - Tax Service $ 85.00 Settement Fee $ - VOE Fee $ 150.00 Total $ 4,415.00 Total $ 8,254.50 Prepaid Interest / Items Potential Additional CostsPer Diem Interest 15 Days $ 1,465.63 Rental 1007 $ 250.00Home Insurance $ 1,800.00 New Survey (if applicable) $ -Flood Insurance $ - 2nd Appraisal / Reinspection $ - Total $ 3,265.63 Total $ 250.00 Escrow and/or Property Taxes Due Total Estimated Monthly PaymentsTotal Insurance(s) 3 Months $ 450.00 Principle and Interest $ 3,343.15Property Taxes 4 Months $ 2,868.64 Total Property Taxes $ 717.16Total $ 3,318.64 Total Insurance(s) $ 150.00 HOA / Maintenance $ - Monthly PMI $ - Total $ 4,210.31Total Estimated CostsEstimated Closing Costs $ 12,919.50 Estimated Escrow Prepaids $ 6,584.27 Estimated Funds To Closing $ 187,003.77

Explaining the reason for the increase and providing some market data to show how rental prices in the area have risen could make things clearer for the tenant.

Hi Matthew,This data is a macro look at median sales price of all property types within those four cities limits.