There will also have to be seasonal maintenance activities such as cleaning of the gutters, emptying water out of the sprinkler systems, etc. to eliminate some of the weather related issues. 

Hi, my name is Rob and I am a 24 year old looking to get a start and dip my toe in the waters of real estate investing.

All that does is slow you down, and quite possibly stop you dead in the water...with no chance to move forward since the are you are investing in won't allow for the reuse of funds.Also, never invest in opportunities.  

Are there factors within my control or specific to my situation that influence this, or is it purely based on lender policy?

I am interested in adding a water feature to a courtyard in a townhouse in the Miami area.Does anyone have a supplier to recommend?

After the housing crash, my long time tenants moved out and I was moving off to grad school, and I could not sell my house (I was way underwater on the mortgage), so I ended up renting it out.I only recently got above water on that house, and it is not the best investment property, but I'm keeping it for now since it is finally generating a positive cash flow.I've recently come into a lot more money (self-employed), and am now in a position to buy even more properties, but I want to do it right this time.

I'm assuming that pre-foreclosures are in the same boat as well.Actually, pre-foreclosures are in more dangerous waters, a short sale the bank just won't go there, screwing around with a foreclosure takes on a blend of federal compliance and consumer issues, cause a delay and you can get nailed.

Electrical, plumbing, exterior paint, hot water heater, refurbish boiler, flat roofs, Windows.

The property has a new bathroom, kitchen, water heater and heating (two years old) he also added a new privacy fence and waterproofed the basement.

Weather or not you put 20% down to avoid PMI is purely a math personal decision that you have to make. there will be some folks that tell you 20% down is better and others that tell you go as low as you can.