As for the deck that is a bit harder to screw up as long as it is sealed properly the rest is just you inspecting upon completion of work, as always get someone licensed and bonded.

I would prioritize finding an accountant who specializes in real estate taxation over one that is local.There are 20+ accountants on this message board who specialize in real estate taxation.

A bit more about us: we run an event based videography company specializing in Ice Skating/Dance but are branching out into wedding and commercial work as well; I have been a career bartender for the past 8 years and I am a huge nerd about food/beverage/hospitality.

That's what I was thinking but if I completed the 1 year of owner occupancy, I would think that I would be free to obtain another one if I wanted to move, regardless of the reason but that must not be how it works even though I'm putting down 15% and not using a special loan program where I'm putting super low down payments such as 3.5% or 5%.

Filing with the state is easy, and you can absolutely do it yourself if you don't need anything special.

Therefore need to get a lien bond.

As others have said, there are cheaper, code-approved ways to accomplish your goal via GFCIs or single point bonding. 

In the mean time I hope that money is in mutual funds, stocks, bonds, CD, or anything that makes a return.

It won't get you any special treatment, but we are friends and it will help you break the ice with him faster.Good luck.

If you want to budget repairs, just put the money saved each month in a special account.