Do you have a nice amount saved up for the activities you enjoy(I assume yes given a 30+ year in Tech plus you mentioning making lots of money already in real estate).If that is the case, what are you looking to achieve now within real estate?

Enjoy man!

I currently enjoy my full time job in health care, but would love to cut down on my hours in another 5-10 years.

Marketing and Advertising: A property manager has the resources and knowledge to effectively market and advertise rental properties, attracting prospective tenants and reducing vacancy periods.In summary, hiring a property manager can streamline operations, enhance profitability, and provide peace of mind for you, allowing you to enjoy your investments rather than being bogged down by day-to-day management tasks.A property manager will give you more time to expand your investment portfolio. 

I don't want to be frugal as to not enjoy life, but also not enjoy too much where I have nothing to show for the future. 

I enjoy helping Bigger Pockets members save time, money and talking REI.  

If this sounds like something that fits you, go for it and make sure to get a property somewhere you can enjoy as well! 

I'm biased because BP Pros get RentRedi for free, but I enjoy it—and I'm currently only renting one property.

Guest checks in, enjoys their stay9. 5 days before check out, auto message for check out instructions are sent10.

Being clear about what’s covered in the lease and by local laws can avoid misunderstandings and set their realistic expectations.If you do plan to carry out the cosmetic upgrades (because the property is overdue and of course you want to ensure your tenants are enjoying their home to the best of your abilities), try to schedule the repairs at times that minimize disruption.