The safe harbor applies to amounts paid during the tax year to acquire or produce what the regs call a “unit of property” (UOP), you must meet these requirements: (1) at the beginning of the tax year, the taxpayer has written accounting procedures treating as an expense for non-tax purposes amounts paid for property costing less than a specified dollar amount (which will be 2500 for you), or with an economic useful life of 12 months or less;.(2) the taxpayer treats the amount paid for the property as an expense on its books and records in accordance with its accounting procedures. ( do this on your bookkeeping software or whatever you utilize)(3) the amount paid for the UOP doesn't exceed $2,500. as substantiated by invoice.Note: The cost for the Unit of Property includes additional costs (for example, delivery fees, installation services, or similar costs) if these additional costs are included on the same invoice with the tangible property.Eg:A purchases 100 printers at $500 each for a total cost of $500,000 as indicated by the invoice.

I am looking to get advice on tax reporting and book keeping, I do have some accounting knowledge already but would like to learn more.

As I understand it, a landlord is required to keep tenants' security deposits in a separate escrow account.  

I have a little over $800 in my Roth IRA but have stopped contributing because I want to save for a down paymentMy Roth IRA is roughly 2.5 years old so it doesn't meet the 5-year exception of using funds for first time home buyersThe rest of my money is in a 90/10 taxable account which is a long-term investment account.

Account Closed  OK don't let the cat out of the bag  although at least they are paying the homes off from govmit.. 

You also need to account for the fact that we are in the Fall/Winter and there are less active buyers looking for a home.

The market data seems very strong but it would be great to get some first hand accounts of how things have been the past year, trends, etc. 

Account Closed  I ended up talking to my contractor and HUD Consultant (this is a 203k loan) and they assured me my risks are minimal. 

Yes, there could be a limitations issue but some jurisdictions permit a significantly longer period to sue on an account.

So any purchase in San Diego with intent to STR should take into account potential STR regulations into any purchasing decision.