You want an accountant who can help you strategize and who is responsive when you want to know the tax consequences of the decisions you are making throughout the year.Good luck.absolutely, yes. we feel confident about filing, but absolutely ignorant to long term tax strategy! 

It really isn't worth it, and the long-term result speak for themselves.

I understand that short-term rentals are only allowed in the Commercial Zone and Historic Core Zone.

He can take a short term bridge up to 75% LTV, payoff the existing loan plus get 22k to fix the foundation up, then sell it at full value.

There's no set point to stop; it depends on your investment goals and tax strategy.Considerations: Consult with a tax professional to tailor this strategy to your specific financial situation, investment goals, and long-term plans.

From an appreciation perspective, over the long-term I don't think one will necessarily outperform the other by a significant margin.

This would be our first rental and I think it could be a good opportunity long-term, but it feels like there’s some red flags here.

I am NOT interested in owning any more real estate (retired here man) so I had planned on just paying my 15% long term Capital Gains tax rate and moving on to my "safe money" retirement program of MYGA's / CD's and High yield Savings account / Bonds / some Stocks.

and long-term relationships to help service my growing portfolio!

It is slightly under rented for the area just slowly trying to raise on long term tenants.