My wife wants to retire to a boutique hotel on a Greek island, maybe 20-25 guests.

Think indy coffee shops, boutique stores, trendy, etc.

Already talked to counselor "boutique" co. that works with people just like me (weeks of searching paid off - these guys don't advertise very well).

Brookside: Located south of the Country Club Plaza, Brookside is a popular neighborhood with a mix of historic homes, trendy restaurants, and boutique shops.

Add on a very supportive principal broker and I feel strongly that I'm able to provide an equivalent or superior level of service as many full-time agents.However, without those competitive advantages of experience and supportive boutique brokerage, I would not feel comfortable with the level of service I could provide.

I have thought about local property management, or part time investment specialist at a boutique real estate brokerage... 

All of them have some sort of clubhouse/pool area, but several of the resort style have lazy rivers, theater rooms, game rooms, on site restaurants, nail salons, boutiques, golf etc.It is very realistic for you to achieve your ROI on a bigger home to net $5k/month after all expenses including HOA, PM at 20%, pool maintenance, utilities, taxes etc.

I work closely with my broker as we are boutique brokerage that specializes in investments specifically STR & co-living.

I run a boutique mortgage brokerage, and read a study from Mailchimp.

We can certainly help you, but just wanted you to know that it is pretty difficult unless you've got the resources to basically buy a boutique hotel.