It's a good practice to overestimate costs and underestimate after-repair values (ARV) to keep your expectations realistic.

By the way - for the same reason the 1st position lien holder will be uneasy with 100% CLTV, as a buyer I would be uneasy with it as well.

I am pretty handy and have done plenty of restoration work myself and not afraid to put in some elbow grease. looking into real estate to get the wealth ball rolling but feel a little uneasy given the current state of the economy. what would you do in my shoes?! 

Keep in mind tax's.

If you’re feeling uneasy about the potential headaches, you might consider a local property manager who specializes in room rentals or shared housing.

I would certainly keep that tenant.

Is it possible to keep my land loan out of it to keep the total cost low?

Assuming these are for short-term loans, such as for flips, @Keith Groshans, you could do what we do and let the borrower keep the money and pay everything when they sell the property.

In my state the standard contract used by realtors addresses this issue by allowing the agent to check a box specifically to limit the seller to keeping the EMD as opposed to going after "liquidated damages" like that.

4) Keep my money in a guaranteed savings account making 4.5%, until rates drop more or something changes, and the numbers are better to make a move?