If you told him you have been playing pickup games for the past year and need help improving your jump shot, now he has evidence you're motivated and a specific goal he can quickly help you work towards.

Are you seeing any emerging trends or opportunities tied to these lifestyle improvements, such as increased demand for certain property types or neighborhoods?

Real estate is a long term wealth building strategy and in that one year you can learn a lot about home improvement and land lording. 

Also, you are totally right, I will approach this one rental at a time to both improve my skills and check is this is for me.

Small improvements or updates can justify slightly higher rents too.

Their previous lease includes a portion of storage in the basement with laundry access(also in basement).Current set up: tenant occupies floor #2 with separate access to the basement for their laundry and storage.Future plan: reno basement and remove storage/laundry access for tenant.

Setting up an LLC and accessing 50k+ in business credit is a simple process that protects your personal finances and positions you to scale faster.

These things need so much power that unless the site has access to major grid access point you're wasting your time. 

They often have access to off-market listings and can also help you navigate on-market listings on MLS.

As the market improves, you might also have a chance to refinance and lower your payments.