Living in the property for two years likely allowed you to claim the capital gains exclusion... up to $250K for singles or $500K if married.

This community is a great place to gain knowledge, connect, and share experiences.

It just feels like I’ve been making a lot of short term sacrifices for long term gains and I have to be really diligent with money management. or I could also just try to borrow money for the renovation, and pay off the line of credit over time, but I feel like that really would limit me and if the stock market(my collateral) went down I could also see some trouble. 

The C rentals still cash flow better, but the difference is marginal and honestly not worth the extra headache. 90% of my gains have been through appreciation and forcing equity through value add.

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. 

But this will also lead to future inflation.The issue is going to be the rich will get richer as they can live with lower cash flow but gain appreciation.

A 1031 exchange would allow you to move into better properties in different locations while indefinitely deferring all tax on gain and depreciation recapture.

We would like to build our own relationships, gain knowledge and find deals.

You'll then see that delinquency rates are:- At their lowest point since 2006- Historically on the low side of normal - On an overall downward trend for the past 4 yearsIn fact, excluding the artificially propped-up mortgage market of 2004-2006 during which delinquency rates were slightly lower than they are today, bottoming out at 1.41% in 2005, there are fewer mortgage delinquencies today than at any time in the past 33 years.By the way, when these scant 1.73% of homeowners become delinquent on their mortgages, they overwhelmingly have the equity to be able to sell the home at a gain if needed.

Maybe lost of tax efficient gains during peak earning years?