Lastly, review Dave Meyer’s The State of Real Estate Investing Report 2024 (in your resource page as a member of BiggerPockets!)

Adding onto what Kieran mentioned above.In the Bay Area in general, and same too in San Jose - it's an appreciation market (properties in San Jose appreciated 12.1% last year).

I have been looking to purchase a second property as an investment for about one year now and it wasn't until last year that I began actually touring multiunits in Chicago and in the Chicagoland suburbs.  

So they are often overstretched with resources to reply to offers or buyers.I think when we last conversed was a few years back.

I've been in SMF for the last 5 years in a nearby market and studying this location for the last 2.

Hey there, I love your predicament because I am currently facing a similar situation, but I will offer my thought and what is motivating my decision. hopefully this could be helpful.we bought during the pandemic and locked in 2.25% rate. last thing I want to do is mess this rate. now with appreciation of almost $200,000 I am wondering what to do especially having created a new llc to focus on STR, flips,BRRRR and home maintenance. in taking this decision I believe you should consider location, which I think from your writeup suggest it's a strong area in terms of appreciation. next question is what market are you looking to invest in STR?

Lastly, one tenant is a headache and we are wondering about offering cash for keys.

Besides, I can offset that risk with requiring first and last month Rent in addition to security deposit.Only Tenants who can submit security deposit and all rent money can sign the lease.

This home was brand new construction so of course there will be general wear and tear on certain items, and I have photos of items they claim are damaged or missing within the 1st month of me moving in along with a walk though video I took on my last day there after I spent a few days cleaning everything.

It's hard to say, so much has changed in the last 2 years it's hard to determine for sure.