Suncontractor vs. employee - pros and cons

[Kenneth LaVoie]

I have a great sub contractor that I may take on as an employee. He appears to be a lifer. (If he can put up with me, that is!) He will be doing things such as:

carpentry
roofing
light plumbing (but no electric)
light landscaping, mowing maybe
actual management (eviction notices, receiving maintenance calls, etc.)
many other unanticipated things I'm sure.

I am a little troubled and hesitant though. With so many "hats" I want to be sure I get the proper worker's comp classifications, etc. I own and manage a lawn care company and it's very simple: mow, trim, prune, mulch, rake, plow and shovel show. Nothing else. Very simple to be "properly insured". With having a "guy friday" tending 49 rental units, it's a little different and I want to be sure I'm not walking into an overly complicated situation.

Do any of you have employees vs. subs? What have you found to be the advantages / disadvantages? Any regrets? unanticipated problems in having an employee??

Also, somewhat unrelated, I thought of possibly taking on a few more places for him to manage. This is probably a bad idea. Managing my own apartments is enough, but I thought if I had another 10 or so units it would keep my man busier, and he would be more likely to stay. I also own and manage a lawn care / landscaping firm so there's some potential synergy here....

Thanks all.