In which case the probability of the IRS examining your return, discovering the grey area issue, taking the opposite position, and winning on appeal would have to be greater than 80% for your expected losses to be higher than just paying it.In their best year ever the IRS is never going to get that probability above 2%At 2%, we are risking an expectation of losing $2.50 by 'going grey' against an expectation of losing $100 by not going into the grey. 

It was nerve wracking, but we pulled of the HELOC while we were under contract and we were able to close after two extensions on the contract. 

I'll be taking my exam in 4 weeks, do you think I should hang my license with a broker and if so, how do I go about finding an investor friendly broker? 

Largely to help talk my nerves down a bit, lol.

Instead of following a blanket rule that any single rental property is a TB, they examined the level of activity and concluded that the rental property generated enough activity to be a TB.

Not necessarily riskier, but definitely a little nervewracking.

I’m currently paying down debt by this summer and should have saved for a relatively small deposit by EOY 2019.Here is my current position.Purchased 1st property as a USDA in MauiUSDA Ln: $400kMortgage: $2202Consumer Debt: $0 (06/2019)Owe Aprx: $385,000Home Value: $500kIncome: $74k yrlyDown payment: $23k (12/2019)720 Credit score Im looking to purchase something small, preferably in a wooded mountain area (ideal for short term rental) but open to anything affordable.Right now I have my short term goals set out but been wracking my brain trying to figure out the next best possible approach to REI.Any help or advice would be GREATLY appreciated!

Examine your intent and act according to the facts. 

It will be much easier if it's month-to-month as you can just give them a notice of termination.If on a year lease you will have to examine the lease and possibly do an eviction for reasons other than non-payment, which is longer and more costly than evictions for non-payment.

@Nancy B.The DMSH is less an expensing election and more a book conformity election.There's a concept involved in the DMSH and other areas of the capital expenditure code section and regs called "units of property".You don't examine each line item on a receipt, you examine "units of property".Buildings are called out under the units of property regs as having special treatment.