Hello @Eric Lyles!
Let me start by saying I love to hear out other people in similar situations: starting out in expensive markets. Since you want to buy and hold, I would suggest you read the book on Rental Property Investing by Brandon Turner (as well as the one on managing tenants by him and his wife). That book summarized a lot of what we hear on the podcasts. Great intro book.
What my partner and I figured out (in our expensive area) is that we have to work backwards from the rent we can get to what our mortgage would be if we purchased the property. We now qualify for more than what we would buy a house because if we bought at our max we would not be able to find tenants to rent at such high price. You need to also consider that if you split up the house (if you are buying single family houses) you may be able to get more rent but then will be managing more people. Also, check with your county for housing regulations of how many unrelated people can live under one roof.
Since you already bought your house maybe you can look at renting to more than one tenant or maybe selling this house (preferably after 2 years so you can defer capital gain taxes) and using the money to buy another one where you look at rents first?
About the taxes, I would talk to my tax preparer. Preparation is key to avoid it becoming something huge at the end of the year.
And about private lenders, it seems like you are in a great financial position, so maybe talk to the lender who gave you the loan on this house about the next house? Or shop around for mortgage brokers and such? No need for higher interest if you qualify for conventional mortgages.
Let me know how everything goes!
