The purchase price of this property was only $170K. 

Purchase price: $205,000 Cash invested: $60,000 This was the first property I purchased.

I am looking into purchasing a second (vacation) home and would love to hear your thought on the pros and cons of going a conventional 30-year second mortgage vs. using a HELOC or Home Equity Loan on my Primary Residence to purchase the second home outright. 

Any advice on how to get the process started would be appreciated. 

So, you can do a land contract for 12 months, which should allow lender to credit you full value of the land vs the purchase price, but the loan will pay off the land contract, so the lender maintains first lien position.Can't help you with the rest of your question, but you should be able to search for "CPA" here on BP to find experts to reach out to.

Regular home purchase or sale?

I work with out-of-state investors and would be happy to share my experience and how I can help you in your next investment purchase.

Part of rent is applied to purchase price. 

I have experience as a Residential agent in Denver, CO and as a commercial Leasing Associate in Chicago, IL.I am planning to purchase my first rental home here in the next year or so and make it my primary residence.

Purchase price: $178,000 Cash invested: $10,000 primary home own use has an Airbnb/ short term rental 5 months out the year/sometime this year will try BRRRR