My goal in real-estate investing is to pursue the buy and hold strategy, particularly with downtown apartments at first (demand for apartment renting in Chicago has been growing in the upper 500,000s by 1-2% annually since 2010).

Can I legally withhold the items and demand payment for them?

This will help keep your personal stuff out of the target of a person that files a legal demand on your business.  

Reasons may include a failure by the landlord to provide peaceful quiet enjoyment of the premises to the tenant, defects in the property, failure on the part of the landlord to make a legally required repair, or a host of other reasons which seem to come out of left field and astound the landlord when the breach occurs and the tenant is demanding a refund of the prepaid rent.

@Brandon LonVelin@Rebecca BelnapI always keep an open mind; however, with what research I have done in the multi famulet market their appears to be a high demand with little supply.

I would actually try to renew her lease for a term so it ended at a high demand time for tenants for your market (and not so she could give 30 day notice in Nov/December).

In Calif that's a whole can of worms on limits, 1099 and liability.Also States have requirements for on site managers: in Calif it's 16 or moreTo get him out, DEMAND a surety bond with you as Also Insured. 

When a servicer auto-dials the wrong number for 30 days, when you email them / call them multiple times to make sure the demand letter is on its way and then they say "oops we forgot, sorry!"

I have seen sites go as high as 220K vacant in medium demand areas.

Obviously, there would be a number of upgrades that would have to be done but assisted living facilities have shown very strong occupancy rates over the last few years and therefore demand is high.Hope this helps.