We exclusively travel during non-peak seasons, so we would be looking to rent out completely during busy/peak seasons, and would stay at the place during slow seasonsQuestions for the experts out there:1. which development(s) tends to be the best for ROI/have the best occupancy rates?

If you pay cash, you don't have a payment, but effectively you are giving up an income stream if the cash had been in a bond or ETF and earning you either interest or appreciation. 

He asked me the following:"I have a paid off rental house that I earn a good chunk of profit on in 2024. 

We let them invest in these homes with us by allowing them to buy a % when they collect/earn enough money.

How much did you really earn on your first flip?

We're relatively new STR owner/operator in Highlands and have been very pleasantly surprised with demand even outside the peak summer season.

If you get your license and join Keller Williams, I would be delighted to be a (long-distance) mentor to you.If real estate interests you (either as an agent, as an investor, or as a skill for future job change), if doesn't hurt to get the training and earn the license. 

They've seen the peaks and valleys (08 crash and now post covid crash) and they've done unbelievably well investing there. 

This creates two loan payments ($100,000 of equity and $300,000 on the new mortgage).Key NumbersHome Equity Loan Interest Rate: 6%Mortgage Interest Rate: 7%Rental Income: $3,000 per monthExpenses (management, taxes, insurance, maintenance): $800 per monthIncome and ExpensesMonthly Rental Income: $3,000Monthly Expenses: $800Monthly Mortgage Payment: $2,000ExplanationThe investor earns $3,000 in rent each month.They pay $2,000 on the investment property mortgage and $800 on other expenses.This leaves $200 profit each month or $2,400 per year.However, you have to pay $6,000 interest on the equity borrowed.This leaves you with an annual loss of $3,600.While the rental property generates positive monthly income, the interest cost of borrowing the initial $100,000 results in an overall loss.

I also have $102k in a money market account that currently earns about 4.5%.