It scares me thinking about trying the Airbnb route but this area has two distinct tourist seasons in the summer and winter so it might be worth it for at least some of the units.

I can fix any issues we can see and know about right away, it’s the hidden ones that older homes just tend to appear.

This exemption can be used every two years.A great wealth-building strategy is to House Hack every two years, live in each house for at least two years, and then sell older House Hacks before the 5-year mark.

It is the most popular software in the industry, and most Tax Preparers are familiar with it, which makes tax season easier.

In off season when its a mid term rental I manage.

The fact of the matter, as @Jay Hinrichs said, is that it *is* an either or proposition at least in the season of growth.

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

Overall though to answer your question, there is some supply glut in the RRG area so those older properties with less amenities are struggling some.

Still strong but lots of competition, so you need to research what works: good pics, seasonal pricing, amenities, etc.

There are a few folks out there encouraging some seasoning.