Multiple people including myself have tried to caution him of the the true costs but he's been repeatedly dismissive and has made it clear we give him motivation and he wants to prove us all wrong (whatever that means). 

We have a member round table discussion on Fridays at 9 am cst.And we have a calendar of events with events from area landlord groups and member meetups.While we are still on zoom we do try to find ways to still be able to connect and talk with each other so our events are not all just another webinar with people talking at you.Hope to connect.

It puts you in a position to learn the market, build connections, and spot deals before most people even know they exist.

Because I rent 4 bedrooms house, it's more conducive to large gatherings and parties.Another issue and please tell me if this is normal that when people book for 5 people they usually have at least 10 or 15 additional guests. 

., Buy early December, on your own or with your spouse be the only housekeeping staff and maintenance people, rent one or two weekends, voila...

DM me if you would like to have a conversation and I can guide you to people I know in the community that could help.

.#2  MINDSET:  Just like some people will NEVER become real estate investors regardless of time, money, related profession, - MOST people will never become real estate investors.   

That's where good people live, and good people make good tenants.But before you put money down on a house, I would find a quality property manager.

I also wouldn't touch hilltop with a 10' pole. struggled. old homes, over budget renovations, lots of issues. realtors push people here since it's the only place cheap houses close to downtown can be good but homes are 1900-1920.

I don't think it will continue to appreciate at that rate forever or honestly past the next few years but right now where prices are in relation to the median housing price of the surrounding market, the need for affordable housing/rents, etc, many people are continuing to flock to the our investment area which is continuing to push the prices of the properties in Chester up closer to the median housing price of the greater area.In regards to inflation, I don't think the inherent value has risen only the demand for the product itself.