This 4-bedroom, 1.5-bath brick bungalow is currently tenanted with a long-term tenant of 5+ years, generating $900 per month on a month-to-month lease.

In Maryland, there is no statewide law that sets a specific limit on late fees in commercial leases.

The lease agreement has a clause that acknowledges that the property is part of an HOA and that tenant indemnifies the landlord from non-performance ("hold harmless" clause).

Are the leases even valid, if they are not signed by you or your property manager? 

This 4-bedroom, 1.5-bath brick bungalow is currently tenanted with a long-term tenant of 5+ years, generating $900 per month on a month-to-month lease.

I've been using various lease option strategies for 30 years. 

Question: what is the $2k for re-leasing costs?

Sometimes condos have stipulations in their deed restrictions that go against doing short term leasing, so I would definitely get your agent or do the research yourself to ensure this isn’t the case at the building you’re looking at.

Setting clear expectations upfront with a detailed lease agreement is a must.Consider Property Management: If managing the property starts feeling overwhelming, consider hiring a property management company, even if just for the rented units.

What is the best way of smoothing the transition and aigning a new lease with increased deposits and rents?