Also in the Danbury area with short term rentals and a few long term rentals. 

@Shyam Subramanyan Yes, you can perform a cost segregation study on your STR properties for the 2023 tax year, even for properties acquired in 2018, 2021, and 2022.

I performed a 1031 exchange last November 2023.

He's is the only member of the HOA.Two units are being rented out as regular annual rentals.Rest are medium term rentals (90 day) for a local hospital.Sp would that mean you can turn it into an apartment building?  

As a first time investor, I'm thinking to replicate those existing houses (with little bit of my touch) but wanted to ask what would be the pros and cons in terms of competing with existing STR's in the community?

We want to live life on our own terms, pursue our passions, and build a future that's truly ours.

@Maxwell Hinesshort term - BRRRR method, for example.buy with cash or hard money, rehab with HELOC money, then refinance and pay it all back.you never want a HELOC as part of a long term situation.

starting by just brokering loans is a good way to start in states that do not require a license.. raising capital from private investors to make loans is a long process And very difficult if you do not have a long track record or pedigree in the industry.. if someone is brand new they really need to go work for a lender first.. other wise IMHO the chance of success is very small.

@Patrick Gray, The first question to ask is if those properties are performing the way you want. 

For example, RentRedi gave us some trouble in refunding a tenant's security deposit and the customer service representatives also notified me that there is currently not a way to refund a tenant's security deposit after 6 months once the deposit is made which concerned us with long term tenants.