If you're considering hard money loans, they can provide fast funding, but with higher interest rates and shorter terms.

Major cities where STRs have only began rising up and gaining public spotlight with the rise of AirBNB are more likely to have more shifting and less stable regulatory environments since those areas are still in the process of trying to find the balance for STRs within their markets. 

For the $525K property, with the low mortgage rate(you will probably never get a such low rate), it might make sense to hold onto it for now, especially if you can still sell it as a primary residence within the next three years and avoid capital gains taxes.

Is this expected since interest rates are high and listing prices are subsequently dropping? 

Look forward to a booming economy, but there's that interest rate thing....

And it doesn't seem to spoil the charm for couples on a romantic getaway.We've been able to raise the nightly rate 2-3x with better occupancy. 

@Jordyn Ohs Assuming your heloc is re-advanceable and the rate is higher than your mortgage, I would suggest you pay your HELOC down as quickly as possible with any cash flow from the properties.

My first mortgage was almost 11% and that was a good rate.

Higher interest rates are keeping some buyers out of the market so properties are sometimes sitting for longer or not getting the desired price. 

Rent rates have increased so quickly over the last few years.