My wife and I spend a lot of time together, we take vacations regularly, and I prioritize my health by working out 3–4 days a week and getting 7–8 hours of sleep most nights.

I can also allow a tenant to grow with me - just moved a family from a two bedroom to a three bedroom apartment.Personally the only reasons I would choose to invest in multiple markets is a) because I wanted an excuse to go somewhere regularly or b) for economic/geographic diversity.I had the advantage that my home market was good.

This is due to bonus depreciation which allows taxpayers to deduct 40% of qualifying property costs in the first year, in addition to regular depreciation for new construction and improvement.

I'm considering investing in STR in Hawaii to diversify my investment portfolio (mainly for capital appreciation) as well as it being a regular vacation place for my family.

Hey Christine, I might be biased, but you could look into Cleveland, Oh.Here are a few things to consider against investing there:- Slower appreciation compared to some other markets- Harsh winters, which can lead to higher maintenance costs- Many discounted single and duplex might need repairs or updates, especially if the previous owners haven’t kept up with maintenance over the years- Some local regulations to be aware of (nothing crazy, but worth noting when trying to close deals).But there are also some solid reasons to invest in Cleveland:- Affordable properties in the $100K-$300K range- Strong long term rental market due to a high rent to price ratio- Landlord friendly laws overall- Potential for great cash flow- Opportunities for Section 8 tenants- stable market once you have the right team in placeEvery market has pros and cons so it comes down to your budget, risk tolerance, and finding a reliable crew you can trust.

If you are organized enough to forsee hang ups and talk with your GC about potential challenges on a regular basis, two brains are better than one.

@David Lewis I'm regularly looking at multi-family listings on MLS and can only find cash flow in tertiary markets - think Lowell, Fitchburg, Springfield, etc.

The investors I have worked with have found it to be a lot easier with the updated technology and everything going through a massive change post covid/2020. 

The hilly terrain is a main reason for this and you can't really see that on a map so knowing the areas is key.We have old housing stock as well so big things like plumbing and electrical can vary cost wise if they have or haven't been updated.

Quote from @Ryan Brown: Good morning,I have a section 8 Tenant that is blasting music from  the evening hours of 6pm to 3am on a regular basis.