I would be interested to see if there's room for added value in finding an underperforming turnkey asset, reducing expenses, pushing rents, improving move-out damage collection, and collecting on other expenses incurred by residents such as utilities, waste-removal, pest control, etc.

I currently own 5 properties as belowCurrent residence: Bought for $637K, downpayment made-126K, current mortgage balance - 500KInvestment Property1: Bought for 175K, downpayment made - 65K, current mortgage balance - 105K, net rental cash per month after PITI+HOA fee payment = $445Investment Property2: Bought for 209K, downpayment made - 72K, current mortgage balance - 124K, net rental cash per month after PITI+HOA fee payment = $436Investment Property3: Bought for 217K, downpayment made - 70K, current mortgage balance - 0, net rental cash per month after PITI+HOA fee payment = $1137Investment Property4: Bought for 455K, downpayment made - 90K, current mortgage balance - 253K, net rental cash per month after PITI+HOA fee payment = $287I also have investments in ETFs worth around 250K.

the home that i live in currently, sits on almost an acre. I am considering putting a tiny house rental on the lot.
thoughts?

I do not know where to get started at all. how to i even go about getting it approved?
...

@Scott LongVirginia will require you to report the rental income from the property in NY because as a Virginia resident, you are required to report world-wide incomeNew York will also require you to report the rental income because the rental property is located in NY.To avoid the "double-taxation", Virginia will provide you a credit for taxes paid(if any) to New York.You are able to withdraw money from the LLC to your personal account.

$400k from a Los Angeles resident's perspective is still "cheap" for a 3+2 SFR.

I'm about to close on a condo for my primary residence and will be looking for my next investment property early next year.

If you tell the residents that since they're paying the heat you're reducing rent by $500/year per unit, then you take in $2k less in rent, but save $3k in heating costs(if my estimate of $5k/yr was right.)

I own one other rental which used to be my primary residence, so this is my first real investment purchase.  

I initially was interested in house hacking, in the Bronx, NY where I currently reside but potential ROI is currently not worthwhile.

As a former Cream City resident, I'm interested in looking at deals there.