Hi ,i'm in the middle of purchasing a vacation rental and called CBIZ and Proper ins,and both companies have a clause about casual workers.not being covered and to have them covered you would need worers comp ins.I sometimes like to hire friends kids to do some painting in my other rentals .but with this commercial type of insurance i guess that's out of the question.Ihad also hoped to ocasionaly hire a local cleaning lady to clean in between bookings.Any advice on what to do would be helpfull .Thanks!

He confessed it had not been properly card for, but that he planned to live another 4 years in the house until his retirement, at which time he suggested I would need to replace it anyway

As a PM I have all the tools to properly screen tenants.  

I'd like to do it to the other side of the house as well but the neighbors have some oversized trees right where it'd be and probably not a fight I want to have to get them removed/ trimmed properly.

You acquire, fix the issue thereby adding value, properly market, and sell for top dollar (relatively).But, if your answer is an external factor beyond possible repair (general area, the manufactured/trailer homes a block away, the major highway with retail/industrial vibe a block in the other direction, etc.), then you're probably better off moving on to the next one.  

Per the lease if it stipulates the landlord has a right to enter the premises with proper notice to perform an inspection of the unit then it's valid.A tenant with a lease cannot keep denying a landlord entry into the property for inspection.

And that includes when I have moved.If he were still living there, I'd have him performing these functions for me. 

do not get carried away, play conservative on your first deal, leave some room for error.3) Find a qualified and experienced contractor, do not settle for cheapest, you want experience here, because their is a significant administrative burden not only paperwork, proper formatting, but also financial constraint on the contractor as these sometimes have $0 prepayment to contractor.

The property will show its age by a bit of deferred maintenance or functional obsolescence.

I would be honest with a reference, but don't give too much information.The questions I usually ask/answer are:  Did tenant give proper notice when leaving?