To renew or to not renew? Options...Recommendations (lease, tenant, renter)

[field3]

My condo tenant is planning to move out in September and is looking to either go with a month to month or 6 month lease. The current lease is set to expire at the end of March.

Currently both the unit and parking leases are in alignment (both ending in April). I like how this is set up as it is easy to keep my dates aligned.

Here are a couple of concerns/challenges:

- My parking is being leased by another user who is willing to go with a 12 month lease at the current going rate.


- What are the opportunity costs with renting it out to a new renter now vs. in September? (Market supply vs. Tenant Demand in those two time frames?)

- How much of a risk would it be to lease both parking and unit out for the same timeframe (6 months) and just have the parking renew at that time again with a slightly higher lease?

- I'm unsure about my current situation where it is an option for me to either move in there or stay where I'm currently at (another condo which I own in the Near West Side) This is fairly flexible.

- Are there any other factors I'm missing out?

[bentlebee]

I never do month to month, only yearly leases and if someone insist then they will have to pay a way higher rent for going month to month...

I don't want to deal with every month waiting if they will stay or move.

So far I only had people renewing againand again until yesterday after 2 years my tenant told me they have to move due to changes in their personal life and I'm helping them find a new place.

There is a shortest to rentals in this area so the rental business is good over here, although in some places you see signs up in the yards from private LL who often are in financial trouble...